Chemistry Heterocyclic Building Blocks Indoles

Indoles

Indole is an organic compound that is both aromatic and heterocyclic, with a chemical formula of C8H7N. Its structure is comprised of a fused five-membered pyrrole ring and a six-membered benzene ring, resulting in a bicyclic configuration.

Indole, which acts as a signal molecule between cells, plays a role in regulating several bacterial physiological processes, such as spore formation, plasmid stability, drug resistance, biofilm creation, and virulence.

Indole, known as Benzopyrrole, is a heterocyclic organic compound present in flower oils like jasmine and orange blossom, coal tar, and fecal matter. Its applications include use in perfumery, production of tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that stimulates root development in plant cuttings.

Indoles are heterocyclic ring systems that have been extensively studied due to their numerous applications in various pathophysiological conditions including cancer, microbial and viral infections, inflammation, depression, migraine, emesis, hypertension, among others.

The involvement of the lone pair of nitrogen in the resonance of the aromatic bicyclic structure gives indole a weak basic character, making it one of the versatile scaffolds in medicinal chemistry.

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By Key Group+−

aminoindole benzoindole benzyloxyindole biindolinylidene boronate-indole bromo-indole-carboxylate bromo-indole-carboxylic-acid bromo-methyl-indole bromoindole chlorindole-carboxylic-acid chloro-indole-carboxylate chloro-methyl indole chloroindole cyanoindole dihydroindolo dimethyl-indole dioxaborolan-indole dioxaborolan-indole-carboxylate fluorindole-carboxylic-acid fluoro-indole-carboxylate fluoroindole fluoromethyl-indole formyl-indole-carboxylate formylindole hydroxyindole hydroxyisoindoline hydroxymethy-indole-carboxylate indol-amine indol-methanamine indol-methanol indol-one indole-boronic-acid indole-carbonitrile indole-ethanol indole-ethylamine indole-hydrochloride indole-hydroxyl indolecarboxylate indolecarboxylic iodo-indole isoindole methanoisoindole methoxy-indole-carboxylate methoxy-methyl-indole methoxyindole methyl-indole-carboxylic-acid methyl-nitro-indole methylindole nitro-indole-carboxylate nitroindole phenyl-indole piperidine-indole pyridinoindole pyrimido-indole trifluoromethyl-indole

By Parent Nucleus+−

Aromatic Heterocycles Benzofurans Indolines Other Aromatic Heterocycles Piperazines Piperidines Pyrazoles Pyridines Pyrimidines Pyrroles Pyrrolidines Pyrrolines

By Functional Group+−

Alcohols Aldehydes Alkenyls Amides Amines Aryls Bromides Carboxylic Acid Salts Carboxylic Acids Chiral Building Blocks Chlorides Esters Ethers Fluorinated Building Blocks Hydrazides Hydrazines Hydroxylamines Iodides Ketones Nitriles Nitroes Organoboron Phenols Sulfamides Sulfides Trifluoromethyls

Framework+−

(1-(tert-butoxycarbonyl)-1H-indol-2-yl)boronic acid (1H-indol-2-yl)boronic acid (1H-indol-2-yl)methanol (3aS,7aS)-octahydro-1H-indole (9H-fluoren-9-yl)methyl (2-(1H-indol-3-yl)ethyl)carbamate 1,2,3,4-tetrahydrocyclopenta[b]indole 1,2-dimethyl-1H-indole 1-(1H-indol-1-yl)ethan-1-one 1-(1H-indol-3-yl)-N,N-dimethylmethanamine 1-(1H-indol-3-yl)ethan-1-one 1-(phenylsulfonyl)-1H-indole 1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine 1-benzyl-1H-indole 1-ethyl-1H-indole 1-methyl-1H-indole 1-methyl-1H-indole-2-carboxylic acid 1-methyl-1H-indole-3-carbaldehyde 1-methyl-1H-pyrrolo[2,3-b]pyridine 1-phenyl-1H-indole 1H-indol-3-ol 1H-indol-3-yl acetate 1H-indol-4-amine 1H-indol-4-ol 1H-indol-5-ol 1H-indol-6-amine 1H-indol-6-ol 1H-indol-7-amine 1H-indole-2-carbaldehyde 1H-indole-2-carbonitrile 1H-indole-3-carbaldehyde 1H-indole-3-carbonitrile 1H-indole-3-carboxylic acid 1H-indole-4-carboxylic acid 1H-indole-5-carbonitrile 1H-indole-5-carboxylic acid 1H-indole-6-carbonitrile 1H-indole-6-carboxylic acid 1H-indole-7-carbonitrile 1H-indole-7-carboxylic acid 1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde 1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 2,3-dimethyl-1H-indole 2-(1,3,2-dioxaborolan-2-yl)-1-methyl-1H-indole 2-(1H-indol-1-yl)acetic acid 2-(1H-indol-3-yl)acetic acid 2-(1H-indol-3-yl)ethan-1-amine 2-(1H-indol-3-yl)ethan-1-ol 2-(2-methyl-1H-indol-3-yl)acetic acid 2-(4-fluorophenyl)-1H-indole 2-methyl-1H-indole-3-carbaldehyde 2-methyl-1H-pyrrolo[2,3-b]pyridine 3-(1-oxoisoindolin-2-yl)piperidine-2,6-dione 3-(1H-indol-3-yl)propanoic acid 3-(piperidin-4-yl)-1H-indole 3-iodo-1H-pyrrolo[2,3-b]pyridine 3-methyl-1H-indole 3H-indole 4-bromo-1H-indole 4-chloro-1H-indole 4-fluoro-1H-indole 4-fluoro-1H-pyrrolo[2,3-b]pyridine 4-fluoroindoline-2,3-dione 4-methoxy-1H-indole 4-methyl-1H-indole 4-nitro-1H-indole 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole 5-(benzyloxy)-1H-indole 5-bromo-1-methyl-1H-indole 5-chloro-1H-indole 5-chloro-1H-indole-2-carboxylic acid 5-chloro-1H-pyrrolo[2,3-b]pyridine 5-fluoro-1H-indole 5-fluoro-1H-pyrrolo[2,3-b]pyridine 5-fluoroindolin-2-one 5-methoxy-1H-indole 5-methoxy-2-methyl-1H-indole 5-methyl-1H-indole 5-nitro-1H-indole 6-(trifluoromethyl)-1H-indole 6-bromo-1-methyl-1H-indole 6-bromo-1H-indole 6-bromo-1H-pyrrolo[2,3-b]pyridine 6-chloro-1H-indole 6-chloro-1H-pyrrolo[2,3-b]pyridine 6-fluoro-1H-indole 6-methoxy-1H-indole 6-methyl-1H-indole 6-methyl-1H-pyrrolo[2,3-b]pyridine 6-nitro-1H-indole 7-bromo-1H-indole 7-bromoindoline-2,3-dione 7-chloro-1H-indole 7-fluoro-1H-indole 7-fluoro-1H-indole-2-carboxylic acid 7-methoxy-1H-indole 7-methyl-1H-indole 7-nitro-1H-indole 9H-pyrido[3,4-b]indole benzo[cd]indol-2(1H)-one ethyl 1H-indole-3-carboxylate ethyl 5-chloro-1H-indole-2-carboxylate ethyl 5-fluoro-1H-indole-2-carboxylate ethyl 6-chloro-1H-indole-2-carboxylate ethyl 7-chloro-1H-indole-2-carboxylate methyl 1H-indole-3-carboxylate methyl 1H-indole-4-carboxylate methyl 1H-indole-5-carboxylate methyl 1H-indole-6-carboxylate methyl 1H-indole-7-carboxylate methyl 2-(1H-indol-3-yl)acetate N-(2-(1H-indol-3-yl)ethyl)acetamide spiro[indoline-3,4'-piperidin]-2-one tert-butyl 1H-indole-1-carboxylate tert-butyl 1H-pyrrolo[2,3-b]pyridine-1-carboxylate tert-butyl 2-(1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate tert-butyl 3-(hydroxymethyl)-1H-indole-1-carboxylate tert-butyl 3-bromo-1H-indole-1-carboxylate tert-butyl 3-iodo-1H-indole-1-carboxylate tert-butyl 5-methoxy-1H-indole-1-carboxylate tryptophan

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    Methyl 6-fluoro-1H-indole-4-carboxylate

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    1,6-Dimethyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

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    1,6-Dimethyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

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    6-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

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    6-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

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    1,5-Dimethyl-1H-indole-2-carbaldehyde

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    1-Methyl-1H-indole-2-carbaldehyde

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    1-Methyl-1H-indole-2-carbaldehyde

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    2-Phenyl-1H-indole

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    1-Methyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

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    1-Methyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

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    Fmoc-Trp-OH

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    tert-Butyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

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    tert-Butyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

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    9H-Pyrido[3,4-b]indole

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    1H-Pyrrolo[2,3-b]pyridine-3-carbaldehyde

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    1H-Pyrrolo[2,3-b]pyridine-3-carbaldehyde

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    1H-Indole

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    2-Methyl-1H-indol-5-ol

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    2-(4-Fluorophenyl)indole

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    1-Ethyl-1H-indole-2-carbaldehyde

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    1-Ethyl-1H-indole-2-carbaldehyde

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    3-(5-Methoxy-1-((4-methoxyphenyl)sulfonyl)-1H-indol-3-yl)propanoic acid

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    3-(5-Methoxy-1-((4-methoxyphenyl)sulfonyl)-1H-indol-3-yl)propanoic acid

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    1-Ethyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

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    1-Ethyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

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    1-Acetyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

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    1-Acetyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

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    4-Methyl-1H-indole-2-carbaldehyde

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    4-Methyl-1H-indole-2-carbaldehyde

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    5-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

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    5-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

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