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Indoles

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Definition: Benzopyrroles with the nitrogen at the number one carbon adjacent to the benzyl portion, in contrast to ISOINDOLES which have the nitrogen away from the six-membered ring.     
Examples Adrenochrome; Alcian Blue; Carbazoles; Carbolines; Cytochalasins; Delavirdine; Gliotoxin; Hydroxytryptophol; Ibogaine; Indapamide; Indican; Indigo Carmine; Indocyanine Green; Indole Alkaloids; Indoleacetic Acids; Indolequinones; Indomethacin; Indoramin; Iprindole; Isatin; Methisazone; Molindone; Oxyphenisatin Acetate; Perindopril; Skatole; Sporidesmins; Tryptamines
 
SubstanceCAS Registry & nameCategoriesSourceDrugs*
dimethylindole red  0   *Carbocyanines *Indoles Fluorescent Dyes. Biochemistry. 2012 Mar 27;51(12):2471-85.
3-ethynyl-5-nitroindolyl-2'-deoxyriboside triphosphate  0   *Indoles *Nucleotides. Nucleic Acids Res. 2012 Mar;40(5):2357-67.
1-(2-(18F)fluoro-3-pyridyl)-4-(2-isopropyl-1-oxo-isoindoline-5-yl)-5-methyl-1H-1,2,3-triazole  0   *Indoles *Triazoles. J Neurochem. 2012 Apr;121(1):115-24
(1H-indol-2-yl)(4-(phenylamino)thieno(2,3-d)pyrimidin-6-yl)methanone  0   *Indoles *Pyrimidines. Bioorg Med Chem. 2012 Jan 1;20(1):125-36
N-(2-(5-hydroxy-1H-indol-3-yl)ethyl)-2-oxopiperidine-3-carboxamide  0   *Indoles *Piperidines. Proc Natl Acad Sci U S A. 2012 Feb 28;109(9):3540-5.
ethyl-6-bromo-5-hydroxy-4-(imidazol-1-yl)-methyl-1-methyl-2-(phenylsulfinylmethyl)-1H-indole-3-carboxylate  0   *Indoles *Sulfoxides. Biomed Chromatogr. 2012 Apr;26(4):458-63.
3-(4-bromobenzyl)-5-(1H-indol-3-yl-methylene)-2-thioxoimidazolidin-4-one  0   *Indoles *Imidazolidines. Int Immunopharmacol. 2011 Nov;11(11):1816-22.
5-(1H-indol-3-yl-methylene)-2-thioxo-imidazolidin-4-one  0   *Indoles *Imidazolidines. Int Immunopharmacol. 2011 Nov;11(11):1816-22.
(4-(3-chloro-4-fluorophenylamino)thieno(2,3-d)pyrimidin-6-yl)(5-hydroxy-1H-indol-2-yl)methanone  0   *Indoles *Pyrimidines. Bioorg Med Chem. 2012 Jan 1;20(1):125-36
(4-(3-chlorophenylamino)thieno(2,3-d)pyrimidin-6-yl)(1H-indol-2-yl)methanone  0   *Indoles *Pyrimidines. Bioorg Med Chem. 2012 Jan 1;20(1):125-36
N-(4-methoxy-3-(4-methylpiperazin-1-yl)phenyl)-1,2-dihydro-3-H-benzo(e)indole-3-carboxamide  0   *Indoles *Piperazines Adrenergic alpha-2 Receptor Antagonists. J Pharmacol Exp Ther. 2012 Mar;340(3):750-64.
(18)F-ICMT11  0   *Azides *Indoles Fluorine Radioisotopes. Bioorg Med Chem Lett. 2011 Dec 1;21(23):6945-9
methyl 5-methoxy-4,5-dihydroindolo(4,3-f,g)quinoline-9-carboxylate  0   *Indoles *Quinolines. Org Lett. 2012 Jan 6;14(1):296-8
6-hydroxyindole  0   *Indoles. Org Biomol Chem. 2012 Jan 14;10(2):267-72
5-(4-bromobenzyloxy)-2-(2-(5-methoxyindolyl)ethyl-1-carbonyl)-4H-chromen-4-one  0   *Chromones *Indoles. J Med Chem. 2012 Jan 26;55(2):966-70.
N-(1-(4-(methylamino)cyclohexyl)indolin-6-yl)thiophene-2-carboximidamide  0   *Indoles *Thiophenes Nitric Oxide Synthase Type I/antagonists & inhibitors. J Med Chem. 2012 Jan 26;55(2):943-55.
N-(cyclopropylsulfonyl)-1-((2,5-difluorophenyl)methyl)-3-(1,2-dihydro-2-oxo-3-pyridinyl)-6-fluoro-5-(methyl)-1H-indole-2-carboxamide  0   *Indoles *Sulfonamides. J Med Chem. 2012 Jan 26;55(2):754-65.
3-(5-carboxypentanoyl)-1-(3-(4-octylphenoxy)-2-oxopropyl)indole-5-carboxylic acid  0   *Indoles Group IV Phospholipases A2/antagonists & inhibitors. Br J Dermatol. 2012 Feb;166(2):306-16
N-((4-fluorophenyl)(1-methyl-1H-imidazol-2-yl)methyl)-2-methyl-3-(1,2,4-thiadiazol-5-yl)-1H-indole-6-carboxamide  0   *Indoles *Thiadiazoles IMP Dehydrogenase/antagonists & inhibitors. Eur J Pharmacol. 2012 Jan 5;674(1):58-63.
neosidomycin  0   *Indoles Deoxyglucose/*analogs & derivatives. J Org Chem. 2011 Dec 2;76(23):9687-98
6-(4-chlorophenyl)-7H-(1,3)dioxolo(4,5-f)indol-7-one-5-oxide  0   *Indoles. J Antimicrob Chemother. 2011 Nov;66(11):2566-72
2-oxocyclopiazonic acid  0   *Indoles. Biosci Biotechnol Biochem. 2011;75(11):2249-52
N-(benzoylphenyl)-5-chloro-1H-indole-2-carboxamide  0   *Indoles. Molecules. 2011;16(10) (dup#14):8292-304
N-(benzoylphenyl)-5-methoxy-1H-indole-2-carboxamide  0   *Indoles. Molecules. 2011;16(10) (dup#14):8292-304
1-(4-benzylpiperidin-1-yl)-2-(6-hydroxy-1H-indol-3-yl)ethane-1,2-dione  0   *Indoles *Piperidines Ligands. J Med Chem. 2011 Dec 22;54(24):8702-6.
2-(4-benzylpiperidin-1-yl)-1-(6-hydroxy-1H-indol-3-yl)ethanone  0   *Indoles *Piperidines Ligands. J Med Chem. 2011 Dec 22;54(24):8702-6.
N-((5-(3-(1-benzylpiperidin-4-yl)propoxy)-1-methyl-1H-indol-2-yl)methyl)-N-methylprop-2-yn-1-amine  0   *Indoles *Piperidines Butyrylcholinesterase Cholinesterase Inhibitors Monoamine Oxidase Inhibitors. J Med Chem. 2011 Dec 22;54(24):8251-70.
omocianine  0   *Carbocyanines *Indoles. Invest Radiol. 2011 Nov;46(11):697-704.
KX1 141  0   *Indoles src-Family Kinases/antagonists & inhibitors. Neurosci Res. 2011 Dec;71(4):348-54.
N-(2-(diethylamino)ethyl)-2-methyl-7-(1,2-dihydro-5-fluoro-2-oxo-3H-indol-3-ylidene)-4,5,6,7-tetrahydro-1H-indole-3-carboxamide  0   *Ethylamines *Indoles. Cancer Chemother Pharmacol. 2012 Jan;69(1):173-83.
3-((4-(3,4-dichlorobenzyl)piperazin-1-yl)methyl)-1H-indole  0   *Indoles *Piperazines. Chem Biol Drug Des. 2011 Nov;78(5):869-75.
4-methoxyindol-3-ylmethylglucosinolate  0   *Glucosinolates *Indoles. New Phytol. 2011 Nov;192(3):713-26
8-methoxy-2,3,4,4a,5,9b-hexahydro-1H-pyrido(4,3-b)indolinium  0   *Indoles *Pyridines. Pharmacol Rep. 2011;63(4):967-74.
3-(4-pyridyl)-1H-indole  0   *Indoles *Pyridines rho-Associated Kinases/antagonists & inhibitors. Development. 2012 Jan;139(2):437-42
5-bromo-3-((3,4,5-trimethoxyphenyl)thio)-1H indole  0   *Indoles Growth Inhibitors. Cell Cycle. 2011 Sep 15;10(18):3208-9
5-((N-benzyl-1H-indol-3-yl)methylene)pyrimidine-2,4,6(1H,3H,5H)trione  0   *Barbiturates *Indoles. Clin Cancer Res. 2011 Oct 15;17(20):6490-9.
PHII-7 compound  0   *Indoles P-Glycoproteins/antagonists & inhibitors. Eur J Pharmacol. 2011 Nov 1;669(1-3):38-44.
ethyl(5-((3-acetyl-1H-indol-1-yl)methyl)-2H-tetrazol-2-yl)acetate  0   *Indoles *Tetrazoles Anti-Infective Agents. Arch Pharm Res. 2011 Jul;34(7):1085-96
1-(1-(2H-tetrazol-5-ylmethyl)-1H-indol-3-yl)ethanone  0   *Indoles *Tetrazoles Anti-Infective Agents. Arch Pharm Res. 2011 Jul;34(7):1085-96
AZD1981  0   *Acetic Acids *Indoles. Bioorg Med Chem Lett. 2011 Nov 1;21(21):6288-92
3-cyclopropylmethyl-7-phenyl-3H-pyrrolo(3,2-f)quinolin-9(6H)-one  0   *Indoles *Quinolones. Biochem Pharmacol. 2012 Jan 1;83(1):16-26.
6-bromoindirubin-3'-(O-(2-morpholin-1-ylethyl)oxime)  0   *Indoles *Oximes Glycogen Synthase Kinase 3/antagonists & inhibitors. J Neurosci Res. 2011 Nov;89(11):1802-11.
6-bromoindirubin-3'-(O-(N,N-diethylcarbamyl)oxime)  0   *Indoles *Oximes Glycogen Synthase Kinase 3/antagonists & inhibitors. J Neurosci Res. 2011 Nov;89(11):1802-11.
psychotripine  0   *Indoles *Pyrroles. Org Lett. 2011 Nov 4;13(21):5896-9
YHHU0895  0   *Indoles *Pyrimidines Antineoplastic Agents. Cancer Lett. 2012 Jan 1;314(1):54-62
2,2'-(1,1'-methylenebis(1H-indole-3,1-diyl))diethanol  0   *Indoles. J Asian Nat Prod Res. 2011 Oct;13(11):1042-6
1-(1- pentyl-1H-indol-3-yl)-2-(2-methoxyphenyl)ethanone  0   *Anisoles *Indoles. J Anal Toxicol. 2011 Sep;35(7):386-93.
(1-hexyl-1H-indol-3-yl)-1-naphthalenylmethanone  0   *Indoles *Naphthalenes. J Anal Toxicol. 2011 Sep;35(7):386-93.
4-(1-(4-fluorobenzyl)-4-hydroxy-1H-indol-3-yl)-2-hydroxy-4-oxobut-2-enoic acid  0   *Hydroxybutyrates *Indoles. Antiviral Res. 2011 Oct;92(1):102-7.
cannabipiperidiethanone  0   *Indoles *Piperidines. Chem Pharm Bull (Tokyo). 2011;59(9):1203-5
1-(2-(5-nitro-1H-indol-2-yl)phenyl)methylpyridinium chloride  0   *Indoles *Pyridinium Compounds. Molecules. 2011;16(9) (dup#20):7627-33
(2-(6-fluoro-1H-indol-3-yl)-ethyl)-(3-(2,2,3,3-tetrafluoropropoxy)benzyl)amine  0   *Benzylamines *Indoles Serotonin Antagonists. Int J Neuropsychopharmacol. 2010 Sep;13(8):1021-33.
(E)-2-(4-(dimethylamino)styryl)-1,3,3-trimethyl-3H-indolium perchlorate  0   *Indoles. J Fluoresc. 2011 Jul;21(4):1713-9
(4-methoxyphenyl)(1-pentyl-1H-indol-3-yl)methanone  0   *Indoles Receptors, Cannabinoid/agonists. Int J Drug Policy. 2011 Jul;22(4):274-7.
AM 694  0   *Indoles Receptors, Cannabinoid/agonists. Int J Drug Policy. 2011 Jul;22(4):274-7.
1-pentyl-3-(2'-chlorophenylacetyl)indole  0   *Indoles Street Drugs. J Anal Toxicol 2011;35(6):360-3
polydopamine  0   *Indoles *Polymers Biocompatible Materials. Nanomedicine (Lond). 2011 Jul;6(5):793-801.
JWH-073  0   *Indoles *Naphthalenes. Anal Chem. 2011 Jun 1;83(11):4228-36
orisuaveoline B  0   *Indoles *Quinazolines. J Nat Prod. 2008 Nov;71(11):1942-5
orisuaveoline A  0   *Indoles *Quinazolines. J Nat Prod. 2008 Nov;71(11):1942-5
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Sources: NLM Medical Subject Headings, NIH UMLS, Drugs@FDA, FDA AERS original data copyright United States Government. No endorsement implied. Last modified 6/6/2012
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