1391:
1945:
2237:
1979:
2015:
408:
267:
1300:
2491:
2268:
2370:
2399:
2022:
2446:
38:
736:
56:
1700:
731:
47:
1207:
957:
2243:
Since the pyrrolic ring is the most reactive portion of indole, electrophilic substitution of the carbocyclic (benzene) ring generally takes place only after N1, C2, and C3 are substituted. A noteworthy exception occurs when electrophilic substitution is carried out in conditions sufficiently acidic
3241:
has previously been identified in the plasma and cerebrospinal fluid of humans, but its functions are not known. ... In kinetic competition experiments using free radical-trapping agents, the capacity of IPA to scavenge hydroxyl radicals exceeded that of melatonin, an indoleamine considered to
3953:
Diels, Otto; Reese, Johannes (1934). "Synthesen in der hydroaromatischen Reihe. XX. Über die
Anlagerung von Acetylen-dicarbonsäureester an Hydrazobenzol" [Syntheses in the hydroaromatic series. XX. The addition of acetylene dicarboxylic acid ester to hydrazobenzene].
2681:
Oswald, Iain W. H.; Paryani, Twinkle R.; Sosa, Manuel E.; Ojeda, Marcos A.; Altenbernd, Mark R.; Grandy, Jonathan J.; Shafer, Nathan S.; Ngo, Kim; Peat, Jack R.; Melshenker, Bradley G.; Skelly, Ian; Koby, Kevin A.; Page, Michael F. Z.; Martin, Thomas J. (2023-10-12).
2037:. Although the synthesis of indole itself is problematic using the Fischer indole synthesis, it is often used to generate indoles substituted in the 2- and/or 3-positions. Indole can still be synthesized, however, using the Fischer indole synthesis by reacting
1989:
is an efficient method of synthesizing indole and substituted indoles. Originally disclosed in a patent in 1976, this method is high-yielding and can generate substituted indoles. This method is especially popular in the
4340:
Kaufman, Teodoro S. (2005). "Synthesis of
Optically-Active Isoquinoline and Indole Alkaloids Employing the Pictet–Spengler Condensation with Removable Chiral Auxiliaries Bound to Nitrogen". In Vicario, J. L. (ed.).
1241:
Certain indole derivatives were important dyestuffs until the end of the 19th century. In the 1930s, interest in indole intensified when it became known that the indole substituent is present in many important
744:
711:
1375:
3242:
be the most potent naturally occurring scavenger of free radicals. In contrast with other antioxidants, IPA was not converted to reactive intermediates with pro-oxidant activity.
2533:
4495:
Schoenherr, H.; Leighton, J. L. (2012). "Direct and Highly
Enantioselective Iso-Pictet-Spengler Reactions with α-Ketoamides: Access to Underexplored Indole Core Structures".
3256:"The van URK-Salkowski reagent — a sensitive and specific chromogenic reagent for silica gel thin-layer chromatographic detection and identification of indole derivatives"
4301:"The intermolecular Pictet–Spengler condensation with chiral carbonyl derivatives in the stereoselective syntheses of optically-active isoquinoline and indole alkaloids"
4158:
Katritzky, Alan R.; Li, Jianqing; Stevens, Christian V. (1995). "Facile
Synthesis of 2-Substituted Indoles and Indolocarbazoles from 2-(Benzotriazol-1-ylmethyl)indole".
1390:
1368:
1944:
3435:"Development and Characterization of Indole-Responsive Whole-Cell Biosensor Based on the Inducible Gene Expression System from Pseudomonas putida KT2440"
1361:
970:
3876:
3155:
Production of IPA was shown to be completely dependent on the presence of gut microflora and could be established by colonization with the bacterium
2585:
1952:
3203:"Potent neuroprotective properties against the Alzheimer beta-amyloid by an endogenous melatonin-related indole structure, indole-3-propionic acid"
4563:
3492:
Ramesh, Deepthi; Joji, Annu; Vijayakumar, Balaji
Gowrivel; Sethumadhavan, Aiswarya; Mani, Maheswaran; Kannan, Tharanikkarasu (15 July 2020).
4185:
Lynch, S. M.; Bur, S. K.; Padwa, A. (2002). "Intramolecular
Amidofuran Cycloadditions across an Indole π-Bond: An Efficient Approach to the
5008:
457:
4259:
Gremmen, C.; Willemse, B.; Wanner, M. J.; Koomen, G.-J. (2000). "Enantiopure
Tetrahydro-β-carbolines via Pictet–Spengler Reactions with
2655:
Purves, Dale; Augustine, George J; Fitzpatrick, David; Katz, Lawrence C; LaMantia, Anthony-Samuel; McNamara, James O; Williams, S Mark.
2236:
1951:
In general, reactions are conducted between 200 and 500 °C. Yields can be as high as 60%. Other precursors to indole include
2393:
results in lithiation exclusively at the C2 position. This strong nucleophile can then be used as such with other electrophiles.
1978:
2063:
3433:
Matulis, Paulius; Kutraite, Ingrida; Augustiniene, Ernesta; Valanciene, Egle; Jonuskiene, Ilona; Malys, Naglis (January 2022).
1986:
1971:
1859:
4485:
4466:
4447:
4350:
2609:
2369:
2108:
2049:
of the formed indole-2-carboxylic acid. This has also been accomplished in a one-pot synthesis using microwave irradiation.
2497:
Despite mediocre yields, intermolecular cycloadditions of indole derivatives have been well documented. One example is the
3551:"Indole-based derivatives as potential antibacterial activity against methicillin-resistance Staphylococcus aureus (MRSA)"
2490:
4556:
2445:
2217:
3893:
3034:"Microbial metabolism of dietary components to bioactive metabolites: opportunities for new therapeutic interventions"
2267:
2014:
4020:
3368:"Bacterial Production of Indole Related Compounds Reveals Their Role in Association Between Duckweeds and Endophytes"
3081:
convert tryptophan to IPA , likely via a tryptophan deaminase. ... IPA also potently scavenges hydroxyl radicals
2950:
2639:
2068:
422:
4530:
3794:
Cacchi, S.; Fabrizi, G. (2005). "Synthesis and
Functionalization of Indoles Through Palladium-catalyzed Reactions".
2405:
Bergman and
Venemalm developed a technique for lithiating the 2-position of unsubstituted indole, as did Katritzky.
2398:
4993:
3301:
Darkoh, Charles; Chappell, Cynthia; Gonzales, Christopher; Okhuysen, Pablo (December 2015). Schloss, P. D. (ed.).
977:
965:
134:
2743:"Analysis of Organic Volatile Flavor Compounds in Fermented Stinky Tofu Using SPME with Different Fiber Coatings"
2117:
1117:
indoles are structural elements of (and for some compounds, the synthetic precursors for) the tryptophan-derived
3604:
Thanikachalam, Punniyakoti
Veeraveedu; Maurya, Rahul Kumar; Garg, Vishali; Monga, Vikramdeep (15 October 2019).
5013:
4998:
4549:
3981:
Huntress, Ernest H.; Bornstein, Joseph; Hearon, William M. (1956). "An Extension of the Diels-Reese Reaction".
692:
4069:
Noland, W. E.; Rush, K. R.; Smith, L. R. (1966). "Nitration of Indoles. IV. The Nitration of 2-Phenylindole".
3771:
2083:
1749:
921:
794:
2794:"The Neuroprotective Effects of Melatonin: Possible Role in the Pathophysiology of Neuropsychiatric Disease"
5003:
4071:
3494:"Indole chalcones: Design, synthesis, in vitro and in silico evaluation against Mycobacterium tuberculosis"
2465:. Intramolecular variants are often higher-yielding than intermolecular cycloadditions. For example, Padwa
2224:. For example, it is alkylated by phosphorylated serine in the biosynthesis of the amino acid tryptophan.
776:
365:
262:
2847:
4232:
Cox, E. D.; Cook, J. M. (1995). "The Pictet-Spengler condensation: a new direction for an old reaction".
2098:
1753:
1549:
386:
3086:
Table 2: Microbial metabolites: their synthesis, mechanisms of action, and effects on health and disease
790:
204:
4012:
Essentials of Organic Chemistry: For Students of Pharmacy, Medicinal Chemistry and Biological Chemistry
2593:
2195:
1110:
735:
604:
580:
3255:
2881:
3090:
Figure 1: Molecular mechanisms of action of indole and its metabolites on host physiology and disease
2103:
2073:
1780:
1512:
274:
3769:
Gribble, G. W. (2000). "Recent developments in indole ring synthesis—methodology and applications".
3089:
4366:
Bonnet, D.; Ganesan, A. (2002). "Solid-Phase Synthesis of Tetrahydro-β-carbolinehydantoins via the
3085:
2498:
2390:
2310:
2225:
2114:
2078:
2058:
2030:
2007:
1846:
Common classical methods applied for the detection of extracellular and environmental indoles, are
403:
4130:
Bergman, J.; Venemalm, L. (1992). "Efficient synthesis of 2-chloro-, 2-bromo-, and 2-iodoindole".
3163:
1796:
1567:
2244:
to exhaustively protonate C3. In this case, C5 is the most common site of electrophilic attack.
2088:
1991:
1792:
1776:
1745:
1574:
1103:
623:
17:
3366:
Gilbert, Sarah; Xu, Jenny; Acosta, Kenneth; Poulev, Alexander; Lebeis, Sarah; Lam, Eric (2018).
152:
3838:
Humphrey, G. R.; Kuethe, J. T. (2006). "Practical Methodologies for the Synthesis of Indoles".
2462:
2381:
After the N–H proton, the hydrogen at C2 is the next most acidic proton on indole. Reaction of
1761:
1723:
1718:
1670:
1473:
1438:
1406:
4535:
4010:
3107:"Metabolomics analysis reveals large effects of gut microflora on mammalian blood metabolites"
2940:
2545:
2121:
1904:
1800:
1530:
1480:
1445:
1015:
758:
723:
1072:. At very low concentrations, however, it has a flowery smell, and is a constituent of many
4783:
4572:
3909:
3716:"Current scenario of indole derivatives with potential anti-drug-resistant cancer activity"
3379:
3314:
3118:
2470:
2228:
2034:
1956:
1862:. For intracellular indole detection and measurement genetically encoded indole-responsive
1855:
1662:
1151:
730:
374:
68:
802:
8:
4901:
4299:
Larghi, Enrique L.; Amongero, Marcela; Bracca, Andrea B. J.; Kaufman, Teodoro S. (2005).
3201:
Chyan YJ, Poeggeler B, Omar RA, Chain DG, Frangione B, Ghiso J, Pappolla MA (July 1999).
2178:
of electrons on the nitrogen atom is not available for protonation. Strong acids such as
2133:
1847:
1824:
1741:
1603:
1539:
1303:
Indole is produced via anthranilate and reacts further to give the amino acid tryptophan.
1283:
224:
110:
100:
3383:
3318:
3122:
2718:
2683:
2029:
One of the oldest and most reliable methods for synthesizing substituted indoles is the
1034:
are derivatives of indole where one or more of the hydrogen atoms have been replaced by
407:
266:
184:
3751:
3696:
3661:"Medicinal chemistry of indole derivatives: Current to future therapeutic prospectives"
3641:
3586:
3531:
3469:
3434:
3410:
3367:
3343:
3303:"A Rapid and Specific Method for the Detection of Indole in Complex Biological Samples"
3302:
3232:
3141:
3106:
3060:
3033:
2820:
2793:
2769:
2742:
2684:"Minor, Nonterpenoid Volatile Compounds Drive the Aroma Differences of Exotic Cannabis"
2418:
2357:
2287:
2093:
1851:
1816:
1705:
1653:
1650:
1503:
1352:
1139:
656:
596:
164:
4098:
4037:
3271:
4861:
4512:
4481:
4462:
4443:
4388:
4346:
4325:
4281:
4214:
4103:
4042:
4016:
3983:
3889:
3856:
3820:
3755:
3743:
3735:
3700:
3688:
3680:
3645:
3633:
3625:
3590:
3578:
3570:
3535:
3523:
3515:
3474:
3456:
3415:
3397:
3348:
3330:
3283:
3275:
3224:
3146:
3065:
2997:
2989:
2984:
2967:
2946:
2825:
2774:
2723:
2705:
2635:
2605:
2353:
2345:
2336:
2179:
1812:
1757:
1676:
1271:
1136:
877:
843:
641:
3606:"An insight into the medicinal perspective of synthetic analogs of indole: A review"
2025:
One-pot microwave-assisted synthesis of indole from phenylhydrazine and pyruvic acid
1712:
by bacteria in the gut. Indole is produced from tryptophan by bacteria that express
814:
4988:
4820:
4504:
4380:
4320:
4310:
4273:
4241:
4206:
4167:
4140:
4112:
4079:
4051:
3991:
3963:
3935:
3881:
3848:
3812:
3804:
3776:
3727:
3672:
3617:
3562:
3505:
3464:
3446:
3405:
3387:
3338:
3322:
3267:
3236:
3214:
3136:
3126:
3055:
3045:
2979:
2921:
2893:
2877:
2859:
2843:
2815:
2805:
2764:
2754:
2713:
2695:
2597:
2251:
2167:
1808:
1765:
1737:
1645:
1639:
1417:
1334:
1286:
molecule between the removal of 3-phospho-glyceraldehyde and the condensation with
1275:
1227:
1177:
1122:
1046:
993:
567:
480:
3549:
Qin, Hua-Li; Liu, Jing; Fang, Wan-Yin; Ravindar, L.; Rakesh, K. P. (15 May 2020).
3077:
spp. convert tryptophan to indole-3-aldehyde (I3A) through unidentified enzymes .
4815:
4315:
4300:
3939:
3731:
3676:
3621:
3566:
3510:
3493:
2590:
Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013
2584:
2046:
2038:
1932:
1804:
1730:
1588:
1494:
1322:
1314:
1247:
786:
668:
293:
3027:
3025:
3023:
3021:
3019:
3017:
3015:
3013:
3011:
1831:
indole, in turn decreasing the concentration of indoxyl sulfate in blood plasma.
338:
4866:
4856:
4810:
4598:
4372:
3926:
Bratulescu, George (2008). "A new and efficient one-pot synthesis of indoles".
3715:
3660:
3605:
3550:
2656:
2514:
2386:
2299:
2295:
2186:
indole. Indole is primarily protonated at the C3, rather than N1, owing to the
2021:
1784:
1630:
1581:
1554:
1333:. A number of indole derivatives have important cellular functions, including
1310:
1299:
1290:. When indole is needed in the cell, it is usually produced from tryptophan by
948:
939:
907:
3050:
2897:
2759:
2344:
complexes tend to react at carbon 3 (see figure below). In analogous fashion,
4982:
4896:
4891:
4871:
4841:
4132:
4116:
4055:
3967:
3885:
3739:
3684:
3629:
3574:
3519:
3460:
3401:
3392:
3334:
3279:
3219:
3202:
3008:
2993:
2863:
2709:
2700:
2510:
2330:
2306:
2255:
1713:
1560:
1426:
1291:
1198:, since indole was first isolated by treatment of the indigo dye with oleum.
556:
546:
255:
3131:
2810:
1924:
Indole and its derivatives can also be synthesized by a variety of methods.
4927:
4516:
4392:
4285:
4218:
3860:
3824:
3747:
3692:
3637:
3582:
3527:
3478:
3419:
3352:
3228:
3175:
3150:
3102:
3069:
3001:
2939:
Stephanopoulos, George; Aristidou, Aristos A.; Nielsen, Jens (1998-10-17).
2829:
2778:
2727:
2326:
2259:
2042:
1899:
1875:
1788:
1681:
1521:
1267:
1159:
849:
2601:
1619:
1206:
4947:
4937:
4932:
4917:
4886:
4659:
3714:
Jia, Yanshu; Wen, Xiaoyue; Gong, Yufeng; Wang, Xuefeng (15 August 2020).
3451:
3326:
3287:
2560:
2550:
2360:
tend to favour attack at the nitrogen, whereas nonpolar solvents such as
2291:
2183:
1895:
1733:
1614:
1466:
1163:
1114:
1092:
1085:
1035:
833:
4541:
4245:
4171:
4144:
4083:
3995:
3816:
2925:
2850:[On the reduction of aromatic compounds by means of zinc dust].
2274:
2262:. It is the precursor to indole-3-acetic acid and synthetic tryptophan.
1744:(PXR) in intestinal cells, thereby facilitating mucosal homeostasis and
806:
798:
244:
4836:
4710:
4705:
4265:
4198:
3840:
3796:
2913:
2502:
2482:
2474:
2314:
2205:
2190:-like reactivity of the portion of the molecule located outside of the
2137:
1995:
1828:
1709:
1609:
1594:
1399:
1279:
1251:
1215:
1182:
1155:
1143:
1118:
1042:
1039:
889:
505:
275:
215:
4508:
4384:
4277:
4210:
3852:
3808:
2525:
Indoles are susceptible to hydrogenation of the imine subunit to give
1807:, a compound that is toxic in high concentrations and associated with
1313:, indole regulates various aspects of bacterial physiology, including
818:
55:
4942:
4922:
4851:
4725:
4720:
4674:
4669:
4649:
4634:
4629:
4624:
3780:
3432:
2555:
2506:
2322:
2175:
2145:
1955:, 2-ethylaniline, and 2-(2-nitrophenyl)ethanol, all of which undergo
1891:
1863:
1598:
1338:
1330:
1132:
1125:
1049:
898:
894:
37:
947:
Except where otherwise noted, data are given for materials in their
46:
4881:
4730:
4715:
4700:
4695:
4664:
4654:
4639:
4593:
2741:
Liu, Yuping; Miao, Zhiwei; Guan, Wei; Sun, Baoguo (26 March 2012).
2526:
2429:
2141:
1936:
1883:
1243:
1231:
1223:
1166:
1081:
1077:
1073:
1038:
groups. Indoles are widely distributed in nature, most notably as
1019:
1012:
926:
912:
868:
313:
235:
3491:
2848:"Ueber die Reduction aromatischer Verbindungen mittelst Zinkstaub"
826:
133:
4963:
4767:
4751:
4746:
4690:
4644:
4619:
4343:
New Methods for the Asymmetric Synthesis of Nitrogen Heterocycles
4305:
2565:
2458:
2361:
2349:
2247:
2231:
of indole will take place at room temperature exclusively at C3.
2221:
2191:
2187:
2171:
2129:
1928:
1913:
1879:
1820:
1326:
1318:
1129:
1027:
1023:
935:
930:
885:
782:
679:
536:
325:
1699:
4876:
4370:-Acyliminium Pictet–Spengler Reaction and Cyclative Cleavage".
3194:
3101:
Wikoff WR, Anfora AT, Liu J, Schultz PG, Lesley SA, Peters EC,
2318:
2125:
1887:
1688:
1287:
1219:
917:
903:
195:
3300:
2938:
2532:
4614:
2478:
2414:
2163:
1772:
1658:
1459:
1255:
1191:
1147:
1065:
1061:
675:
349:
175:
123:
3603:
2968:"Indole as an intercellular signal in microbial communities"
2485:. Indoles also undergo intramolecular and cycloadditions.
1214:
Indole chemistry began to develop with the study of the dye
391:
4298:
4258:
2341:
1909:
1756:
to the brain, IPA confers a neuroprotective effect against
1235:
1069:
561:
253 to 254 °C (487 to 489 °F; 526 to 527 K)
526:
304:
4345:. Thiruvananthapuram: Research SignPost. pp. 99–147.
2654:
2204:
of −3.6. The sensitivity of many indolic compounds (e.g.,
1803:
for AhR. Indole can also be metabolized by the liver into
2208:) under acidic conditions is caused by this protonation.
862:
551:
52 to 54 °C (126 to 129 °F; 325 to 327 K)
2413:
Due to the electron-rich nature of indole, it is easily
768:
531:
Fecal or jasmine like (at extremely low concentrations)
4129:
3980:
3200:
2132:. With other solvents, other products are formed: with
3100:
2680:
1113:, mainly at position 3 (see diagram in right margin).
3365:
2477:
intermediates. In this case, the 2-aminofuran is the
2275:
N–H acidity and organometallic indole anion complexes
2250:, a useful synthetic intermediate, is produced via a
1965:
1783:(AhR) in intestinal immune cells, in turn increasing
3168:
2911:
Van Order, R. B.; Lindwall, H. G. (1942). "Indole".
2305:
and water-free conditions are required for complete
2174:, the aromatic character of the ring means that the
1874:
Indoles and their derivatives are promising against
1722:
metabolizes tryptophan into indole and subsequently
1344:
1258:), and it remains an active area of research today.
1146:. Other indolic compounds include the plant hormone
1055:
3659:Kumari, Archana; Singh, Rajesh K. (1 August 2019).
2942:
Metabolic Engineering: Principles and Methodologies
2376:
4494:
4157:
3548:
1064:at room temperature. It occurs naturally in human
764:
4531:Synthesis of indoles (overview of recent methods)
2910:
2586:International Union of Pure and Applied Chemistry
2052:
1998:are made up of specifically substituted indoles.
1238:dust. In 1869, he proposed a formula for indole.
151:
4980:
4480:. Vol. 10. Stuttgart: Thieme. p. 361.
1902:, bacterial infections of methicillin-resistant
337:
4068:
2876:
2152:
1278:. It is an intermediate in the biosynthesis of
109:
4456:
3877:Ullmann's Encyclopedia of Industrial Chemistry
3837:
3713:
3094:
2886:Berichte der Deutschen Chemischen Gesellschaft
2740:
2634:(4th ed.). New York: W. H. Freeman.
822:
4557:
4365:
4184:
3793:
2220:is C3, which is 10 times more reactive than
2211:
1369:
431:InChI=1S/C8H7N/c1-2-4-8-7(3-1)5-6-9-8/h1-6,9H
3831:
2313:derivatives can react in two ways. The more
2128:gives dimethyl indole-2,3-dicarboxylate and
1708:(indole and certain other derivatives) from
1261:
1210:Baeyer's original structure for indole, 1869
441:InChI=1/C8H7N/c1-2-4-8-7(3-1)5-6-9-8/h1-6,9H
4123:
4035:
3762:
3658:
3439:International Journal of Molecular Sciences
3031:
2904:
2625:
2623:
2621:
2452:
2001:
4564:
4550:
4090:
4062:
3952:
3925:
3787:
2959:
2630:Nelson, David L.; Cox, Michael M. (2005).
1376:
1362:
810:
406:
265:
223:
4571:
4324:
4314:
4178:
4096:
4029:
3509:
3468:
3450:
3409:
3391:
3342:
3218:
3140:
3130:
3059:
3049:
2983:
2870:
2836:
2819:
2809:
2768:
2758:
2717:
2699:
2629:
2216:The most reactive position on indole for
373:
4437:
4428:
2618:
2020:
1565:
1537:
1298:
1205:
1022:structure, consisting of a six-membered
4476:Joule, J. (2000). E. J., Thomas (ed.).
4339:
4231:
4225:
3874:Collin, Gerd; Höke, Hartmut. "Indole".
3768:
3720:European Journal of Medicinal Chemistry
3610:European Journal of Medicinal Chemistry
3555:European Journal of Medicinal Chemistry
3498:European Journal of Medicinal Chemistry
1869:
1704:This diagram shows the biosynthesis of
402:
243:
14:
4981:
4015:. John Wiley & Sons. p. 143.
4008:
3873:
3307:Applied and Environmental Microbiology
3253:
2965:
2842:
2408:
1927:The main industrial routes start from
1686:
1667:
1636:
1625:
1579:
1572:
1544:
1517:
1510:
1501:
1492:
1485:
1478:
1471:
1457:
1450:
1443:
1436:
1095:on a larger molecule, it is called an
1084:. It is the main volatile compound in
838:121 °C (250 °F; 394 K)
256:
4545:
4475:
4422:
1775:) species metabolize tryptophan into
1586:
1528:
1464:
1424:
1415:
1404:
1135:, as well as the naturally occurring
434:Key: SIKJAQJRHWYJAI-UHFFFAOYSA-N
203:
183:
4036:James, P. N.; Snyder, H. R. (1959).
2966:Lee, Jin-Hyung; Lee, Jintae (2010).
2648:
1841:
1397:
573:0.19 g/100 ml (20 °C)
5009:Heterocyclic compounds with 2 rings
4536:Synthesis and properties of indoles
2791:
2218:electrophilic aromatic substitution
1919:
444:Key: SIKJAQJRHWYJAI-UHFFFAOYAI
328:
312:
24:
3956:Justus Liebig's Annalen der Chemie
3032:Zhang LS, Davies SS (April 2016).
2531:
1987:Leimgruber–Batcho indole synthesis
1972:Leimgruber–Batcho indole synthesis
1966:Leimgruber–Batcho indole synthesis
1787:(IL-22) production. Indole itself
25:
5025:
4524:
4461:. Oxford, UK: Blackwell Science.
2792:Lee, Jung Goo (21 October 2019).
2109:Baeyer–Emmerling indole synthesis
2069:Cadogan-Sundberg indole synthesis
1353:human gastrointestinal microbiota
1056:General properties and occurrence
4457:Joule, J. A.; Mills, K. (2000).
2985:10.1111/j.1574-6976.2009.00204.x
2852:Annalen der Chemie und Pharmacie
2657:"Olfactory Perception in Humans"
2520:
2489:
2444:
2424:will selectively oxidize indole
2397:
2377:Carbon acidity and C2 lithiation
2368:
2329:at nitrogen-1, whereas the more
2266:
2235:
2194:ring. The protonated form has a
2064:Bischler–Möhlau indole synthesis
2013:
1977:
1943:
1698:
1389:
955:
734:
729:
498:
492:
54:
45:
36:
4433:. New York: Wiley Interscience.
4399:
4359:
4333:
4292:
4252:
4151:
4097:Heaney, H.; Ley, S. V. (1974).
4002:
3974:
3946:
3919:
3902:
3867:
3707:
3652:
3597:
3542:
3485:
3426:
3359:
3294:
3247:
2945:. Academic Press. p. 251.
2932:
2884:[Synthesis of indole].
2118:dimethyl acetylenedicarboxylate
951:(at 25 °C , 100 kPa).
4009:Dewick, Paul M. (2013-03-20).
2785:
2734:
2674:
2661:Olfactory Perception in Humans
2594:The Royal Society of Chemistry
2578:
2509:, which produces a mixture of
2053:Other indole-forming reactions
1931:via vapor-phase reaction with
1121:alkaloids, which includes the
1026:ring fused to a five-membered
1011:. Indole is classified as an
693:Occupational safety and health
486:
13:
1:
4442:. San Diego: Academic Press.
4429:Houlihan, W. J., ed. (1972).
3772:J. Chem. Soc. Perkin Trans. 1
3272:10.1016/S0021-9673(00)89300-0
2572:
2325:compounds tend to react with
2084:Hemetsberger indole synthesis
1627:Maintains mucosal reactivity:
1311:intercellular signal molecule
1218:. Indigo can be converted to
1158:, the anti-inflammatory drug
4316:10.3998/ark.5550190.0006.c09
3940:10.1016/j.tetlet.2007.12.015
3732:10.1016/j.ejmech.2020.112359
3677:10.1016/j.bioorg.2019.103021
3622:10.1016/j.ejmech.2019.07.019
3567:10.1016/j.ejmech.2020.112245
3511:10.1016/j.ejmech.2020.112358
3111:Proc. Natl. Acad. Sci. U.S.A
2481:, whereas the indole is the
2153:Chemical reactions of indole
1994:, where many pharmaceutical
1282:, where it stays inside the
1080:. It has been identified in
7:
3260:Journal of Chromatography A
3254:Ehmann, Axel (1977-02-11).
2539:
2157:
2099:Nenitzescu indole synthesis
10:
5030:
2632:Principles of Biochemistry
2417:. Simple oxidants such as
2212:Electrophilic substitution
2005:
1969:
1201:
1111:electrophilic substitution
4956:
4910:
4829:
4803:
4796:
4776:
4760:
4739:
4683:
4607:
4586:
4579:
4326:2027/spo.5550190.0006.c09
4309:. RL-1554K (12): 98–153.
3180:Human Metabolome Database
3051:10.1186/s13073-016-0296-x
2972:FEMS Microbiology Reviews
2898:10.1002/cber.186900201268
2760:10.3390/molecules17043708
2104:Reissert indole synthesis
2074:Fukuyama indole synthesis
1781:aryl hydrocarbon receptor
1351:Tryptophan metabolism by
1262:Biosynthesis and function
1068:and has an intense fecal
945:
854:
710:
690:
685:
634:
473:
453:
418:
93:
86:2,3-Benzopyrrole, ketole,
83:
67:
62:
53:
44:
35:
4438:Sundberg, R. J. (1996).
4263:-Sulfinyl Tryptamines".
4117:10.15227/orgsyn.054.0058
4056:10.15227/orgsyn.039.0030
3968:10.1002/jlac.19345110114
3886:10.1002/14356007.a14_167
3393:10.3389/fchem.2018.00265
3220:10.1074/jbc.274.31.21937
3176:"3-Indolepropionic acid"
2880:; Emmerling, A. (1869).
2864:10.1002/jlac.18661400306
2701:10.1021/acsomega.3c04496
2517:of the desired product.
2499:Pictet-Spengler reaction
2461:of indole is capable of
2453:Cycloadditions of indole
2391:lithium diisopropylamide
2385:-protected indoles with
2079:Gassman indole synthesis
2059:Bartoli indole synthesis
2031:Fischer indole synthesis
2008:Fischer indole synthesis
2002:Fischer indole synthesis
1779:(I3A) which acts on the
1150:(indolyl-3-acetic acid,
777:Precautionary statements
541:1.1747 g/cm, solid
4994:Foul-smelling chemicals
3880:. Weinheim: Wiley-VCH.
3182:. University of Alberta
3132:10.1073/pnas.0812874106
2811:10.3390/brainsci9100285
2463:cycloaddition reactions
2124:to an adduct, which in
2089:Larock indole synthesis
2033:, developed in 1883 by
1992:pharmaceutical industry
1793:glucagon-like peptide-1
1752:from the intestine and
1729:(IPA), a highly potent
1104:systematic nomenclature
624:Magnetic susceptibility
4459:Heterocyclic Chemistry
4407:Tetrahedron: Asymmetry
3372:Frontiers in Chemistry
3164:IPA metabolism diagram
3157:Clostridium sporogenes
3079:Clostridium sporogenes
2536:
2279:The N–H center has a p
2026:
1789:triggers the secretion
1719:Clostridium sporogenes
1671:chronic kidney disease
1304:
1211:
5014:Nitrogen heterocycles
4999:Simple aromatic rings
4573:Simple aromatic rings
2882:"Synthese des Indols"
2602:10.1039/9781849733069
2546:Indole-3-butyric acid
2535:
2513:, leading to reduced
2333:magnesium compounds (
2122:1,2-diphenylhydrazine
2024:
1905:Staphylococcus aureus
1302:
1209:
575:Soluble in hot water
4784:Cyclooctadecanonaene
4538:at chemsynthesis.com
4478:Science of Synthesis
3665:Bioorganic Chemistry
3452:10.3390/ijms23094649
3327:10.1128/AEM.02787-15
2471:Diels-Alder reaction
2469:have developed this
2115:Diels–Reese reaction
1870:Medical applications
1546:Mucosal homeostasis:
1076:. It also occurs in
69:Preferred IUPAC name
5004:Perfume ingredients
4902:5-Aza-7-deazapurine
4405:Zhu, G.; Zhang, X.
4246:10.1021/cr00038a004
4172:10.1021/jo00116a026
4145:10.1021/jo00034a058
4084:10.1021/jo01339a013
4038:"Indole-3-aldehyde"
3996:10.1021/ja01591a055
3928:Tetrahedron Letters
3384:2018FrCh....6..265G
3319:2015ApEnM..81.8093D
3213:(31): 21937–21942.
3123:2009PNAS..106.3698W
2926:10.1021/cr60095a004
2694:(42): 39203–39216.
2409:Oxidation of indole
2340:) and (especially)
2134:glacial acetic acid
1935:in the presence of
1858:reagent assays and
1762:Alzheimer's disease
1742:pregnane X receptor
1740:. IPA binds to the
1706:bioactive compounds
1604:4-Hydroxy-2-nonenal
1323:resistance to drugs
1284:tryptophan synthase
568:Solubility in water
513: g·mol
465:C12=C(C=CN2)C=CC=C1
165:Beilstein Reference
32:
4423:General references
2537:
2364:favour C3 attack.
2317:salts such as the
2094:Madelung synthesis
2027:
1817:activated charcoal
1797:intestinal L cells
1651:Smooth muscle cell
1305:
1212:
1140:dimethyltryptamine
996:with the formula
978:Infobox references
855:Related compounds
30:
4976:
4975:
4972:
4971:
4862:Benzo(c)thiophene
4792:
4791:
4509:10.1021/ol300922b
4487:978-3-13-112241-4
4468:978-0-632-05453-4
4449:978-0-12-676945-6
4385:10.1021/cc020026h
4352:978-81-7736-278-7
4278:10.1021/ol006034t
4272:(13): 1955–1958.
4211:10.1021/ol027024q
4166:(11): 3401–3404.
4104:Organic Syntheses
4043:Organic Syntheses
3984:J. Am. Chem. Soc.
3853:10.1021/cr0505270
3809:10.1021/cr040639b
3313:(23): 8093–8097.
3117:(10): 3698–3703.
2611:978-0-85404-182-4
2473:to form advanced
2422:-bromosuccinimide
2337:Grignard reagents
2180:hydrochloric acid
1842:Detection methods
1838:
1837:
1819:), an intestinal
1813:renal dysfunction
1777:indole-3-aldehyde
1758:cerebral ischemia
1738:hydroxyl radicals
1725:3-indolepropionic
1677:Renal dysfunction
1385:
1357:
1335:neurotransmitters
1272:shikimate pathway
1226:. Then, in 1866,
1137:psychedelic drugs
1109:Indole undergoes
1091:When indole is a
986:Chemical compound
984:
983:
844:Safety data sheet
759:Hazard statements
706:Skin sensitising
642:Crystal structure
387:CompTox Dashboard
135:Interactive image
27:Chemical compound
16:(Redirected from
5021:
4821:Trithiapentalene
4801:
4800:
4584:
4583:
4566:
4559:
4552:
4543:
4542:
4520:
4491:
4472:
4453:
4434:
4431:Indoles Part One
4417:
4403:
4397:
4396:
4363:
4357:
4356:
4337:
4331:
4330:
4328:
4318:
4296:
4290:
4289:
4256:
4250:
4249:
4240:(6): 1797–1842.
4234:Chemical Reviews
4229:
4223:
4222:
4182:
4176:
4175:
4155:
4149:
4148:
4127:
4121:
4120:
4099:"1-Benzylindole"
4094:
4088:
4087:
4066:
4060:
4059:
4033:
4027:
4026:
4006:
4000:
3999:
3978:
3972:
3971:
3950:
3944:
3943:
3923:
3917:
3916:
3914:
3906:
3900:
3899:
3871:
3865:
3864:
3847:(7): 2875–2911.
3835:
3829:
3828:
3803:(7): 2873–2920.
3791:
3785:
3784:
3781:10.1039/a909834h
3766:
3760:
3759:
3711:
3705:
3704:
3656:
3650:
3649:
3601:
3595:
3594:
3546:
3540:
3539:
3513:
3489:
3483:
3482:
3472:
3454:
3430:
3424:
3423:
3413:
3395:
3363:
3357:
3356:
3346:
3298:
3292:
3291:
3251:
3245:
3244:
3222:
3198:
3192:
3191:
3189:
3187:
3172:
3166:
3161:
3144:
3134:
3098:
3092:
3083:
3063:
3053:
3029:
3006:
3005:
2987:
2963:
2957:
2956:
2936:
2930:
2929:
2908:
2902:
2901:
2874:
2868:
2867:
2840:
2834:
2833:
2823:
2813:
2789:
2783:
2782:
2772:
2762:
2753:(4): 3708–3722.
2738:
2732:
2731:
2721:
2703:
2678:
2672:
2671:
2669:
2667:
2652:
2646:
2645:
2627:
2616:
2615:
2582:
2568:(3-methylindole)
2505:derivatives and
2493:
2448:
2401:
2372:
2309:. The resulting
2270:
2252:Mannich reaction
2239:
2166:, indole is not
2017:
1981:
1947:
1920:Synthetic routes
1809:vascular disease
1766:Lactobacillaceae
1746:barrier function
1726:
1702:
1701:
1691:
1684:
1669:Associated with
1665:
1646:Oxidative stress
1640:vascular disease
1638:Associated with
1634:
1623:
1622:fibril formation
1584:
1577:
1570:
1563:
1542:
1535:
1526:
1515:
1508:
1506:
1499:
1490:
1483:
1476:
1469:
1462:
1455:
1448:
1441:
1434:
1422:
1413:
1402:
1393:
1383:
1378:
1371:
1364:
1355:
1345:
1248:indole alkaloids
1234:to indole using
1228:Adolf von Baeyer
1123:neurotransmitter
1047:neurotransmitter
1010:
994:organic compound
968:
962:
959:
958:
828:
824:
820:
816:
812:
808:
804:
800:
796:
792:
788:
784:
770:
766:
738:
733:
630:-85.0·10 cm/mol
512:
500:
494:
488:
481:Chemical formula
411:
410:
395:
393:
377:
341:
330:
316:
294:Gmelin Reference
277:
269:
258:
247:
227:
207:
187:
155:
137:
113:
58:
49:
40:
33:
29:
21:
5029:
5028:
5024:
5023:
5022:
5020:
5019:
5018:
4979:
4978:
4977:
4968:
4952:
4906:
4825:
4816:Thienothiophene
4788:
4772:
4756:
4735:
4679:
4603:
4575:
4570:
4527:
4488:
4469:
4450:
4425:
4420:
4404:
4400:
4364:
4360:
4353:
4338:
4334:
4297:
4293:
4257:
4253:
4230:
4226:
4183:
4179:
4156:
4152:
4128:
4124:
4095:
4091:
4067:
4063:
4034:
4030:
4023:
4007:
4003:
3979:
3975:
3951:
3947:
3924:
3920:
3912:
3908:
3907:
3903:
3896:
3872:
3868:
3836:
3832:
3792:
3788:
3767:
3763:
3712:
3708:
3657:
3653:
3602:
3598:
3547:
3543:
3490:
3486:
3431:
3427:
3364:
3360:
3299:
3295:
3252:
3248:
3199:
3195:
3185:
3183:
3174:
3173:
3169:
3162:
3099:
3095:
3088:
3084:
3030:
3009:
2964:
2960:
2953:
2937:
2933:
2909:
2905:
2875:
2871:
2841:
2837:
2790:
2786:
2739:
2735:
2679:
2675:
2665:
2663:
2653:
2649:
2642:
2628:
2619:
2612:
2596:. p. 213.
2583:
2579:
2575:
2542:
2523:
2457:Only the C2–C3
2455:
2411:
2379:
2290:, so that very
2285:
2277:
2254:of indole with
2226:Vilsmeier–Haack
2214:
2202:
2160:
2155:
2055:
2047:decarboxylation
2039:phenylhydrazine
2010:
2004:
1974:
1968:
1962:
1953:formyltoluidine
1933:ethylene glycol
1922:
1872:
1866:is applicable.
1844:
1839:
1834:
1833:
1832:
1805:indoxyl sulfate
1736:that scavenges
1731:neuroprotective
1724:
1703:
1695:
1694:
1693:
1692:
1687:
1685:
1679:
1674:
1668:
1666:
1656:
1648:
1643:
1637:
1635:
1628:
1626:
1624:
1617:
1612:
1607:
1601:
1593:↓Activation of
1592:
1589:Neuroprotectant
1587:
1585:
1580:
1578:
1573:
1571:
1566:
1564:
1558:
1552:
1547:
1545:
1543:
1538:
1536:
1532:
1529:
1527:
1523:
1520:
1518:
1516:
1511:
1509:
1504:
1502:
1500:
1496:
1493:
1491:
1486:
1484:
1479:
1477:
1472:
1470:
1465:
1463:
1458:
1456:
1451:
1449:
1444:
1442:
1437:
1435:
1432:
1430:
1425:
1423:
1419:
1416:
1414:
1409:
1405:
1403:
1398:
1394:
1386:
1382:
1329:formation, and
1264:
1204:
1058:
1009:
1005:
1001:
997:
987:
980:
975:
974:
973: ?)
964:
960:
956:
952:
934:
925:
916:
911:
902:
893:
882:
879:
865:
779:
761:
747:
726:
703:
671:
659:
657:Molecular shape
650:
644:
627:
613:
594:
589:
574:
570:
510:
497:
491:
483:
469:
466:
461:
460:
449:
446:
445:
442:
436:
435:
432:
426:
425:
414:
396:
389:
380:
360:
344:
331:
319:
296:
287:
250:
230:
210:
190:
167:
158:
140:
127:
116:
103:
89:
87:
79:
78:
28:
23:
22:
15:
12:
11:
5:
5027:
5017:
5016:
5011:
5006:
5001:
4996:
4991:
4974:
4973:
4970:
4969:
4967:
4966:
4960:
4958:
4954:
4953:
4951:
4950:
4945:
4940:
4935:
4930:
4925:
4920:
4914:
4912:
4908:
4907:
4905:
4904:
4899:
4894:
4889:
4884:
4879:
4874:
4869:
4867:Benzophosphole
4864:
4859:
4857:Benzothiophene
4854:
4849:
4844:
4839:
4833:
4831:
4827:
4826:
4824:
4823:
4818:
4813:
4811:Diazapentalene
4807:
4805:
4798:
4794:
4793:
4790:
4789:
4787:
4786:
4780:
4778:
4774:
4773:
4771:
4770:
4764:
4762:
4758:
4757:
4755:
4754:
4749:
4743:
4741:
4740:Seven-membered
4737:
4736:
4734:
4733:
4728:
4723:
4718:
4713:
4708:
4703:
4698:
4693:
4687:
4685:
4681:
4680:
4678:
4677:
4672:
4667:
4662:
4657:
4652:
4647:
4642:
4637:
4632:
4627:
4622:
4617:
4611:
4609:
4605:
4604:
4602:
4601:
4599:Cyclopropenone
4596:
4590:
4588:
4587:Three-membered
4581:
4577:
4576:
4569:
4568:
4561:
4554:
4546:
4540:
4539:
4533:
4526:
4525:External links
4523:
4522:
4521:
4503:(10): 2610–3.
4492:
4486:
4473:
4467:
4454:
4448:
4435:
4424:
4421:
4419:
4418:
4398:
4379:(6): 546–548.
4373:J. Comb. Chem.
4358:
4351:
4332:
4291:
4251:
4224:
4205:(26): 4643–5.
4177:
4150:
4122:
4089:
4061:
4028:
4021:
4001:
3973:
3945:
3918:
3901:
3895:978-3527306732
3894:
3866:
3830:
3786:
3761:
3706:
3651:
3596:
3541:
3484:
3425:
3358:
3293:
3266:(2): 267–276.
3246:
3193:
3167:
3105:(March 2009).
3093:
3007:
2958:
2951:
2931:
2903:
2869:
2858:(3): 295–296.
2835:
2798:Brain Sciences
2784:
2733:
2673:
2647:
2640:
2617:
2610:
2576:
2574:
2571:
2570:
2569:
2563:
2558:
2553:
2548:
2541:
2538:
2522:
2519:
2495:
2494:
2454:
2451:
2450:
2449:
2410:
2407:
2403:
2402:
2378:
2375:
2374:
2373:
2303:-butyl lithium
2296:sodium hydride
2283:
2276:
2273:
2272:
2271:
2241:
2240:
2213:
2210:
2200:
2182:can, however,
2159:
2156:
2154:
2151:
2150:
2149:
2111:
2106:
2101:
2096:
2091:
2086:
2081:
2076:
2071:
2066:
2061:
2054:
2051:
2019:
2018:
2006:Main article:
2003:
2000:
1983:
1982:
1970:Main article:
1967:
1964:
1949:
1948:
1921:
1918:
1871:
1868:
1843:
1840:
1836:
1835:
1825:taken by mouth
1799:and acts as a
1785:interleukin-22
1697:
1696:
1661:thickness and
1396:
1395:
1388:
1387:
1381:
1380:
1373:
1366:
1358:
1350:
1349:
1348:
1343:
1307:
1306:
1268:biosynthesized
1263:
1260:
1203:
1200:
1057:
1054:
1007:
1003:
999:
985:
982:
981:
976:
954:
953:
949:standard state
946:
943:
942:
940:benzophosphole
908:benzothiophene
883:
875:
872:
871:
866:
860:
857:
856:
852:
851:
847:
840:
839:
836:
830:
829:
780:
775:
772:
771:
762:
757:
754:
753:
748:
743:
740:
739:
727:
722:
719:
718:
708:
707:
704:
701:
698:
697:
688:
687:
683:
682:
672:
667:
664:
663:
660:
655:
652:
651:
648:
645:
640:
637:
636:
632:
631:
628:
622:
619:
618:
615:
611:
601:
600:
591:
587:
577:
576:
571:
566:
563:
562:
559:
553:
552:
549:
543:
542:
539:
533:
532:
529:
523:
522:
519:
515:
514:
508:
502:
501:
495:
489:
484:
479:
476:
475:
471:
470:
468:
467:
464:
456:
455:
454:
451:
450:
448:
447:
443:
440:
439:
437:
433:
430:
429:
421:
420:
419:
416:
415:
413:
412:
399:
397:
385:
382:
381:
379:
378:
370:
368:
362:
361:
359:
358:
354:
352:
346:
345:
343:
342:
334:
332:
324:
321:
320:
318:
317:
309:
307:
301:
300:
297:
292:
289:
288:
286:
285:
281:
279:
271:
270:
260:
252:
251:
249:
248:
240:
238:
232:
231:
229:
228:
220:
218:
212:
211:
209:
208:
200:
198:
192:
191:
189:
188:
180:
178:
172:
171:
168:
163:
160:
159:
157:
156:
148:
146:
142:
141:
139:
138:
130:
128:
121:
118:
117:
115:
114:
106:
104:
99:
96:
95:
91:
90:
85:
81:
80:
72:
71:
65:
64:
60:
59:
51:
50:
42:
41:
26:
9:
6:
4:
3:
2:
5026:
5015:
5012:
5010:
5007:
5005:
5002:
5000:
4997:
4995:
4992:
4990:
4987:
4986:
4984:
4965:
4962:
4961:
4959:
4955:
4949:
4946:
4944:
4941:
4939:
4936:
4934:
4931:
4929:
4926:
4924:
4921:
4919:
4916:
4915:
4913:
4909:
4903:
4900:
4898:
4897:Benzothiazole
4895:
4893:
4892:Benzisoxazole
4890:
4888:
4885:
4883:
4880:
4878:
4875:
4873:
4872:Benzimidazole
4870:
4868:
4865:
4863:
4860:
4858:
4855:
4853:
4850:
4848:
4845:
4843:
4842:Isobenzofuran
4840:
4838:
4835:
4834:
4832:
4828:
4822:
4819:
4817:
4814:
4812:
4809:
4808:
4806:
4802:
4799:
4795:
4785:
4782:
4781:
4779:
4775:
4769:
4766:
4765:
4763:
4761:Nine-membered
4759:
4753:
4750:
4748:
4745:
4744:
4742:
4738:
4732:
4729:
4727:
4724:
4722:
4719:
4717:
4714:
4712:
4709:
4707:
4704:
4702:
4699:
4697:
4694:
4692:
4689:
4688:
4686:
4682:
4676:
4673:
4671:
4668:
4666:
4663:
4661:
4658:
4656:
4653:
4651:
4648:
4646:
4643:
4641:
4638:
4636:
4633:
4631:
4628:
4626:
4623:
4621:
4618:
4616:
4613:
4612:
4610:
4608:Five-membered
4606:
4600:
4597:
4595:
4592:
4591:
4589:
4585:
4582:
4578:
4574:
4567:
4562:
4560:
4555:
4553:
4548:
4547:
4544:
4537:
4534:
4532:
4529:
4528:
4518:
4514:
4510:
4506:
4502:
4498:
4493:
4489:
4483:
4479:
4474:
4470:
4464:
4460:
4455:
4451:
4445:
4441:
4436:
4432:
4427:
4426:
4415:
4411:
4408:
4402:
4394:
4390:
4386:
4382:
4378:
4375:
4374:
4369:
4362:
4354:
4348:
4344:
4336:
4327:
4322:
4317:
4312:
4308:
4307:
4302:
4295:
4287:
4283:
4279:
4275:
4271:
4268:
4267:
4262:
4255:
4247:
4243:
4239:
4235:
4228:
4220:
4216:
4212:
4208:
4204:
4201:
4200:
4195:
4192:
4188:
4181:
4173:
4169:
4165:
4161:
4154:
4146:
4142:
4138:
4135:
4134:
4133:J. Org. Chem.
4126:
4118:
4114:
4110:
4106:
4105:
4100:
4093:
4085:
4081:
4077:
4074:
4073:
4072:J. Org. Chem.
4065:
4057:
4053:
4049:
4045:
4044:
4039:
4032:
4024:
4022:9781118681961
4018:
4014:
4013:
4005:
3997:
3993:
3989:
3986:
3985:
3977:
3969:
3965:
3961:
3957:
3949:
3941:
3937:
3933:
3929:
3922:
3911:
3905:
3897:
3891:
3887:
3883:
3879:
3878:
3870:
3862:
3858:
3854:
3850:
3846:
3843:
3842:
3834:
3826:
3822:
3818:
3814:
3810:
3806:
3802:
3799:
3798:
3790:
3782:
3778:
3774:
3773:
3765:
3757:
3753:
3749:
3745:
3741:
3737:
3733:
3729:
3725:
3721:
3717:
3710:
3702:
3698:
3694:
3690:
3686:
3682:
3678:
3674:
3670:
3666:
3662:
3655:
3647:
3643:
3639:
3635:
3631:
3627:
3623:
3619:
3615:
3611:
3607:
3600:
3592:
3588:
3584:
3580:
3576:
3572:
3568:
3564:
3560:
3556:
3552:
3545:
3537:
3533:
3529:
3525:
3521:
3517:
3512:
3507:
3503:
3499:
3495:
3488:
3480:
3476:
3471:
3466:
3462:
3458:
3453:
3448:
3444:
3440:
3436:
3429:
3421:
3417:
3412:
3407:
3403:
3399:
3394:
3389:
3385:
3381:
3377:
3373:
3369:
3362:
3354:
3350:
3345:
3340:
3336:
3332:
3328:
3324:
3320:
3316:
3312:
3308:
3304:
3297:
3289:
3285:
3281:
3277:
3273:
3269:
3265:
3261:
3257:
3250:
3243:
3238:
3234:
3230:
3226:
3221:
3216:
3212:
3208:
3207:J. Biol. Chem
3204:
3197:
3181:
3177:
3171:
3165:
3160:
3158:
3152:
3148:
3143:
3138:
3133:
3128:
3124:
3120:
3116:
3112:
3108:
3104:
3097:
3091:
3087:
3082:
3080:
3076:
3075:Lactobacillus
3071:
3067:
3062:
3057:
3052:
3047:
3043:
3039:
3035:
3028:
3026:
3024:
3022:
3020:
3018:
3016:
3014:
3012:
3003:
2999:
2995:
2991:
2986:
2981:
2978:(4): 426–44.
2977:
2973:
2969:
2962:
2954:
2952:9780080536286
2948:
2944:
2943:
2935:
2927:
2923:
2919:
2916:
2915:
2907:
2899:
2895:
2891:
2887:
2883:
2879:
2873:
2865:
2861:
2857:
2853:
2849:
2845:
2839:
2831:
2827:
2822:
2817:
2812:
2807:
2803:
2799:
2795:
2788:
2780:
2776:
2771:
2766:
2761:
2756:
2752:
2748:
2744:
2737:
2729:
2725:
2720:
2715:
2711:
2707:
2702:
2697:
2693:
2689:
2685:
2677:
2662:
2658:
2651:
2643:
2641:0-7167-4339-6
2637:
2633:
2626:
2624:
2622:
2613:
2607:
2603:
2599:
2595:
2591:
2587:
2581:
2577:
2567:
2564:
2562:
2559:
2557:
2554:
2552:
2549:
2547:
2544:
2543:
2534:
2530:
2528:
2521:Hydrogenation
2518:
2516:
2512:
2511:diastereomers
2508:
2504:
2500:
2492:
2488:
2487:
2486:
2484:
2480:
2476:
2472:
2468:
2464:
2460:
2447:
2443:
2442:
2441:
2439:
2435:
2431:
2427:
2423:
2421:
2416:
2406:
2400:
2396:
2395:
2394:
2392:
2388:
2387:butyl lithium
2384:
2371:
2367:
2366:
2365:
2363:
2359:
2355:
2351:
2347:
2343:
2339:
2338:
2332:
2328:
2327:electrophiles
2324:
2320:
2316:
2312:
2311:organometalic
2308:
2307:deprotonation
2304:
2302:
2297:
2293:
2289:
2282:
2269:
2265:
2264:
2263:
2261:
2257:
2256:dimethylamine
2253:
2249:
2245:
2238:
2234:
2233:
2232:
2230:
2227:
2223:
2219:
2209:
2207:
2203:
2199:
2193:
2189:
2185:
2181:
2177:
2173:
2169:
2165:
2147:
2143:
2139:
2135:
2131:
2127:
2123:
2119:
2116:
2112:
2110:
2107:
2105:
2102:
2100:
2097:
2095:
2092:
2090:
2087:
2085:
2082:
2080:
2077:
2075:
2072:
2070:
2067:
2065:
2062:
2060:
2057:
2056:
2050:
2048:
2044:
2040:
2036:
2032:
2023:
2016:
2012:
2011:
2009:
1999:
1997:
1993:
1988:
1980:
1976:
1975:
1973:
1963:
1960:
1958:
1954:
1946:
1942:
1941:
1940:
1938:
1934:
1930:
1925:
1917:
1915:
1911:
1907:
1906:
1901:
1897:
1893:
1889:
1885:
1881:
1877:
1867:
1865:
1861:
1857:
1853:
1849:
1830:
1826:
1822:
1818:
1814:
1810:
1806:
1802:
1798:
1794:
1790:
1786:
1782:
1778:
1774:
1771:
1770:Lactobacillus
1767:
1763:
1759:
1755:
1751:
1747:
1743:
1739:
1735:
1732:
1728:
1721:
1720:
1715:
1714:tryptophanase
1711:
1707:
1690:
1683:
1678:
1672:
1664:
1663:calcification
1660:
1655:
1654:proliferation
1652:
1647:
1641:
1632:
1621:
1616:
1611:
1605:
1600:
1596:
1590:
1583:
1576:
1569:
1562:
1556:
1551:
1541:
1534:
1525:
1514:
1507:
1498:
1489:
1482:
1475:
1468:
1461:
1454:
1447:
1440:
1428:
1427:Tryptophanase
1421:
1412:
1411:
1401:
1392:
1379:
1374:
1372:
1367:
1365:
1360:
1359:
1354:
1347:
1346:
1342:
1340:
1336:
1332:
1328:
1324:
1320:
1316:
1312:
1301:
1297:
1296:
1295:
1293:
1292:tryptophanase
1289:
1285:
1281:
1277:
1273:
1269:
1259:
1257:
1253:
1249:
1245:
1239:
1237:
1233:
1229:
1225:
1221:
1217:
1208:
1199:
1197:
1196:
1194:
1188:
1187:
1185:
1180:of the words
1179:
1175:
1170:
1168:
1165:
1161:
1157:
1153:
1149:
1145:
1141:
1138:
1134:
1131:
1127:
1124:
1120:
1116:
1112:
1107:
1105:
1101:
1099:
1094:
1089:
1087:
1083:
1079:
1075:
1071:
1067:
1063:
1053:
1051:
1048:
1044:
1041:
1037:
1033:
1029:
1025:
1021:
1017:
1014:
995:
991:
979:
972:
967:
950:
944:
941:
937:
932:
928:
923:
919:
914:
909:
905:
900:
896:
891:
887:
884:
881:
874:
873:
870:
867:
864:
859:
858:
853:
850:
848:
845:
842:
841:
837:
835:
832:
831:
781:
778:
774:
773:
763:
760:
756:
755:
752:
749:
746:
742:
741:
737:
732:
728:
725:
721:
720:
716:
714:
709:
705:
700:
699:
695:
694:
689:
684:
681:
677:
673:
670:
669:Dipole moment
666:
665:
661:
658:
654:
653:
646:
643:
639:
638:
633:
629:
625:
621:
620:
616:
610:
606:
603:
602:
598:
592:
586:
582:
579:
578:
572:
569:
565:
564:
560:
558:
557:Boiling point
555:
554:
550:
548:
547:Melting point
545:
544:
540:
538:
535:
534:
530:
528:
525:
524:
520:
517:
516:
509:
507:
504:
503:
485:
482:
478:
477:
472:
463:
462:
459:
452:
438:
428:
427:
424:
417:
409:
405:
404:DTXSID0020737
401:
400:
398:
388:
384:
383:
376:
372:
371:
369:
367:
364:
363:
356:
355:
353:
351:
348:
347:
340:
336:
335:
333:
327:
323:
322:
315:
311:
310:
308:
306:
303:
302:
298:
295:
291:
290:
283:
282:
280:
278:
273:
272:
268:
264:
261:
259:
257:ECHA InfoCard
254:
253:
246:
242:
241:
239:
237:
234:
233:
226:
222:
221:
219:
217:
214:
213:
206:
202:
201:
199:
197:
194:
193:
186:
182:
181:
179:
177:
174:
173:
169:
166:
162:
161:
154:
150:
149:
147:
144:
143:
136:
132:
131:
129:
125:
120:
119:
112:
108:
107:
105:
102:
98:
97:
92:
82:
76:
70:
66:
61:
57:
52:
48:
43:
39:
34:
19:
4957:Five + Seven
4928:Isoquinoline
4846:
4684:Six-membered
4500:
4496:
4477:
4458:
4439:
4430:
4413:
4409:
4406:
4401:
4376:
4371:
4367:
4361:
4342:
4335:
4304:
4294:
4269:
4264:
4260:
4254:
4237:
4233:
4227:
4202:
4197:
4193:
4190:
4187:Aspidosperma
4186:
4180:
4163:
4160:J. Org. Chem
4159:
4153:
4136:
4131:
4125:
4108:
4102:
4092:
4075:
4070:
4064:
4047:
4041:
4031:
4011:
4004:
3990:(10): 2225.
3987:
3982:
3976:
3959:
3955:
3948:
3931:
3927:
3921:
3904:
3875:
3869:
3844:
3839:
3833:
3817:11573/232340
3800:
3795:
3789:
3770:
3764:
3723:
3719:
3709:
3668:
3664:
3654:
3613:
3609:
3599:
3558:
3554:
3544:
3501:
3497:
3487:
3442:
3438:
3428:
3375:
3371:
3361:
3310:
3306:
3296:
3263:
3259:
3249:
3240:
3210:
3206:
3196:
3184:. Retrieved
3179:
3170:
3156:
3154:
3114:
3110:
3096:
3078:
3074:
3073:
3041:
3037:
2975:
2971:
2961:
2941:
2934:
2917:
2912:
2906:
2889:
2885:
2872:
2855:
2851:
2838:
2804:(285): 285.
2801:
2797:
2787:
2750:
2746:
2736:
2691:
2687:
2676:
2664:. Retrieved
2660:
2650:
2631:
2589:
2580:
2524:
2496:
2466:
2456:
2437:
2433:
2425:
2419:
2412:
2404:
2382:
2380:
2334:
2300:
2292:strong bases
2280:
2278:
2260:formaldehyde
2246:
2242:
2215:
2197:
2170:: just like
2162:Unlike most
2161:
2120:reacts with
2045:followed by
2043:pyruvic acid
2035:Emil Fischer
2028:
1984:
1961:
1957:cyclizations
1950:
1926:
1923:
1903:
1900:hypertension
1876:tuberculosis
1873:
1845:
1769:
1754:distribution
1748:. Following
1717:
1682:Uremic toxin
1487:
1452:
1407:
1308:
1276:anthranilate
1265:
1240:
1222:and then to
1213:
1192:
1190:
1183:
1181:
1173:
1171:
1160:indomethacin
1108:
1097:
1096:
1090:
1060:Indole is a
1059:
1031:
989:
988:
922:methylindole
750:
712:
702:Main hazards
691:
608:
584:
521:White solid
350:RTECS number
94:Identifiers
84:Other names
74:
4948:Phthalazine
4938:Quinazoline
4933:Quinoxaline
4918:Naphthalene
4887:Benzoxazole
4804:Five + Five
4777:18-membered
4660:Isothiazole
4139:(8): 2495.
3910:"Indol NSP"
3775:(7): 1045.
3616:: 562–612.
3445:(9): 4649.
2892:: 679–682.
2561:Isoindoline
2551:Indole test
2229:formylation
2206:tryptamines
2140:, and with
1912:) and even
1896:convulsions
1815:. AST-120 (
1795:(GLP-1) in
1734:antioxidant
1659:Aortic wall
1615:Antioxidant
1595:glial cells
1408:Clostridium
1321:stability,
1317:formation,
1246:, known as
1178:portmanteau
1164:betablocker
1115:Substituted
1093:substituent
1086:stinky tofu
1036:substituent
1018:. It has a
1016:heterocycle
834:Flash point
745:Signal word
696:(OHS/OSH):
518:Appearance
474:Properties
263:100.004.019
205:ChEMBL15844
185:CHEBI:16881
88:1-benzazole
4983:Categories
4837:Benzofuran
4830:Five + Six
4711:Pyridazine
4706:Pyrimidine
4266:Org. Lett.
4199:Org. Lett.
3934:(6): 984.
3841:Chem. Rev.
3797:Chem. Rev.
3726:: 112359.
3671:: 103021.
3561:: 112245.
3504:: 112358.
3038:Genome Med
2914:Chem. Rev.
2878:Baeyer, A.
2844:Baeyer, A.
2666:20 October
2573:References
2503:tryptophan
2483:dienophile
2475:strychnine
2138:pyrazolone
1750:absorption
1710:tryptophan
1633:production
1618:–Inhibits
1610:DNA damage
1599:astrocytes
1533:epithelium
1531:Intestinal
1519:Intestinal
1431:expressing
1410:sporogenes
1400:Tryptophan
1280:tryptophan
1266:Indole is
1252:tryptophan
1162:, and the
1156:tryptophol
1144:psilocybin
1119:tryptamine
1043:tryptophan
1040:amino acid
890:benzofuran
724:Pictograms
674:2.11
635:Structure
506:Molar mass
375:8724FJW4M5
216:ChemSpider
122:3D model (
101:CAS Number
4943:Cinnoline
4923:Quinoline
4911:Six + Six
4852:Isoindole
4726:Pentazine
4721:Tetrazine
4675:Pentazole
4670:Tetrazole
4650:Isoxazole
4635:Phosphole
4630:Thiophene
4625:Imidazole
4497:Org. Lett
4191:Strychnos
4078:: 65–69.
3756:219021072
3740:0223-5234
3701:182950054
3685:0045-2068
3646:198911553
3630:0223-5234
3591:214695328
3575:0223-5234
3536:218490655
3520:0223-5234
3461:1422-0067
3402:2296-2646
3335:0099-2240
3280:0021-9673
3103:Siuzdak G
3044:(1): 46.
2994:0168-6445
2920:: 69–96.
2747:Molecules
2710:2470-1343
2688:ACS Omega
2556:Isoindole
2527:indolines
2507:aldehydes
2323:potassium
2286:of 21 in
2184:protonate
2176:lone pair
2146:quinoline
1937:catalysts
1892:migraines
1864:biosensor
1856:Ehrlich’s
1848:Salkowski
1620:β-amyloid
1339:serotonin
1331:virulence
1244:alkaloids
1172:The name
1133:melatonin
1126:serotonin
1050:serotonin
899:carboline
895:carbazole
880:compounds
799:P302+P352
795:P301+P312
715:labelling
595:(21.0 in
357:NL2450000
284:204-420-7
276:EC Number
4882:Indazole
4731:Hexazine
4716:Triazine
4701:Pyrazine
4696:Pyridine
4665:Triazole
4655:Thiazole
4640:Pyrazole
4594:Borirene
4517:22540677
4393:12425597
4286:10891200
4219:12489950
3861:16836303
3825:16011327
3748:32531682
3693:31176854
3638:31344615
3583:32220687
3528:32361610
3479:35563040
3420:30050896
3353:26386049
3229:10419516
3151:19234110
3070:27102537
3002:20070374
2846:(1866).
2830:31640239
2779:22450681
2728:37901519
2719:10601067
2588:(2014).
2540:See also
2501:between
2430:oxindole
2415:oxidized
2352:such as
2350:solvents
2348:aprotic
2331:covalent
2294:such as
2158:Basicity
2142:pyridine
1884:diabetes
1823:that is
1557:protein-
1555:Junction
1433:bacteria
1337:such as
1232:oxindole
1230:reduced
1224:oxindole
1167:pindolol
1128:and the
1082:cannabis
1078:coal tar
1074:perfumes
1020:bicyclic
1013:aromatic
927:oxindole
913:indoline
878:aromatic
876:Related
869:Indolium
686:Hazards
626:(χ)
605:Basicity
236:DrugBank
111:120-72-9
4989:Indoles
4964:Azulene
4797:2 rings
4768:Azonine
4752:Tropone
4747:Borepin
4691:Benzene
4645:Oxazole
4620:Pyrrole
4440:Indoles
4416:, 2415.
4306:Arkivoc
4196:Core".
3962:: 168.
3470:9105386
3411:6052042
3380:Bibcode
3378:: 265.
3344:4651089
3315:Bibcode
3237:6630247
3186:12 June
3142:2656143
3119:Bibcode
3061:4840492
2821:6826722
2770:6268145
2566:Skatole
2459:pi bond
2362:toluene
2335:indole
2248:Gramine
2222:benzene
2192:benzene
2188:enamine
2172:pyrrole
2130:aniline
2113:In the
1929:aniline
1914:viruses
1880:malaria
1829:adsorbs
1821:sorbent
1689:Kidneys
1559:coding
1505:AST-120
1497:sulfate
1495:Indoxyl
1420:bacilli
1327:biofilm
1319:plasmid
1270:in the
1250:(e.g.,
1202:History
1130:hormone
1098:indolyl
1032:Indoles
1028:pyrrole
1024:benzene
971:what is
969: (
936:skatole
931:pyrrole
886:benzene
863:cations
680:benzene
662:Planar
581:Acidity
537:Density
511:117.151
326:PubChem
245:DB04532
170:107693
77:-Indole
31:Indole
18:Indoles
4877:Purine
4847:Indole
4580:1 ring
4515:
4484:
4465:
4446:
4391:
4349:
4284:
4217:
4111:: 58.
4050:: 30.
4019:
3892:
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3823:
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3738:
3699:
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3644:
3636:
3628:
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3467:
3459:
3418:
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3351:
3341:
3333:
3288:188858
3286:
3278:
3235:
3227:
3149:
3139:
3068:
3058:
3000:
2992:
2949:
2828:
2818:
2777:
2767:
2726:
2716:
2708:
2638:
2608:
2467:et al.
2319:sodium
2164:amines
2126:xylene
1888:cancer
1852:Kovács
1801:ligand
1606:levels
1568:L cell
1522:immune
1488:Indole
1453:Indole
1418:Lacto-
1309:As an
1288:serine
1256:auxins
1220:isatin
1216:indigo
1174:indole
1030:ring.
992:is an
990:Indole
966:verify
963:
918:isatin
904:indene
861:Other
846:(SDS)
751:Danger
458:SMILES
314:C00463
196:ChEMBL
153:B01251
145:3DMet
63:Names
4615:Furan
3913:(PDF)
3752:S2CID
3697:S2CID
3642:S2CID
3587:S2CID
3532:S2CID
3233:S2CID
2515:yield
2479:diene
2346:polar
2315:ionic
2168:basic
2041:with
1996:drugs
1631:IL-22
1575:GLP-1
1561:mRNAs
1550:TNF-α
1524:cells
1467:Brain
1460:Liver
1315:spore
1176:is a
1148:auxin
1100:group
1066:feces
1062:solid
617:17.6
423:InChI
299:3477
176:ChEBI
124:JSmol
4513:PMID
4482:ISBN
4463:ISBN
4444:ISBN
4410:1998
4389:PMID
4347:ISBN
4282:PMID
4215:PMID
4194:ABCE
4189:and
4017:ISBN
3890:ISBN
3857:PMID
3821:PMID
3744:PMID
3736:ISSN
3689:PMID
3681:ISSN
3634:PMID
3626:ISSN
3579:PMID
3571:ISSN
3524:PMID
3516:ISSN
3475:PMID
3457:ISSN
3416:PMID
3398:ISSN
3349:PMID
3331:ISSN
3284:PMID
3276:ISSN
3225:PMID
3188:2018
3147:PMID
3066:PMID
2998:PMID
2990:ISSN
2947:ISBN
2826:PMID
2775:PMID
2724:PMID
2706:ISSN
2668:2020
2636:ISBN
2606:ISBN
2529:.
2436:and
2358:DMSO
2356:and
2342:zinc
2288:DMSO
2258:and
1985:The
1910:MRSA
1860:HPLC
1811:and
1773:s.l.
1760:and
1727:acid
1597:and
1274:via
1254:and
1236:zinc
1189:and
1142:and
1070:odor
1045:and
1006:CCNH
827:P501
823:P405
819:P363
815:P361
811:P330
807:P322
803:P312
791:P280
787:P270
783:P264
769:H311
765:H302
647:Pna2
597:DMSO
593:16.2
527:Odor
366:UNII
305:KEGG
4505:doi
4381:doi
4321:hdl
4311:doi
4274:doi
4242:doi
4207:doi
4168:doi
4141:doi
4113:doi
4080:doi
4052:doi
3992:doi
3964:doi
3960:511
3936:doi
3882:doi
3849:doi
3845:106
3813:hdl
3805:doi
3801:105
3777:doi
3728:doi
3724:200
3673:doi
3618:doi
3614:180
3563:doi
3559:194
3506:doi
3502:198
3465:PMC
3447:doi
3406:PMC
3388:doi
3339:PMC
3323:doi
3268:doi
3264:132
3215:doi
3211:274
3137:PMC
3127:doi
3115:106
3056:PMC
3046:doi
2980:doi
2922:doi
2894:doi
2860:doi
2856:140
2816:PMC
2806:doi
2765:PMC
2755:doi
2714:PMC
2696:doi
2598:doi
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