2124-55-2

Basic information

• Product Name: Indole-4-carboxylic acid
• Synonyms: INDOLE-4-CARBOXYLIC ACID;1H-INDOLE-4-CARBOXYLIC ACID;1H-4-INDOLECARBOXYLIC ACID;4-INDOLECARBOXYLIC ACID;4-CARBOXYINDOLE;RARECHEM AL BE 1201;Indole-4-Carbocylic acid;4-INDOLE CARBOXYLIC ACIDINDOLE-4-CARBOXYLIC ACID
• CAS NO: 2124-55-2
• Molecular Formula: C₉H₇NO₂
• Molecular Weight: 161.16
• EINECS: 1312995-182-4
• Product Categories: blocks;Carboxes;IndolesOxindoles;Indole/indoline/oxindole;Indole and Indoline;Indoles and derivatives;Indole;Indoles;Simple Indoles;Building Blocks;Heterocyclic Building Blocks;Heterocycle-Indole series
• Mol File: 2124-55-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 213-214 °C(lit.)
• Boiling Point: 213-214℃
• Flash Point: 207.6 °C
• Appearance: Beige/Powder
• Density: 1.408 g/cm³
• Vapor Pressure: 8.6E-08mmHg at 25°C
• Storage Temp.: Keep Cold
• PKA: 3.90±0.10(Predicted)
• CAS DataBase Reference: Indole-4-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Indole-4-carboxylic acid(2124-55-2)
• EPA Substance Registry System: Indole-4-carboxylic acid(2124-55-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 2124-55-2(Hazardous Substances Data)

Usage

Chemical Properties

Beige powder

Uses

Reactant for preparation of substituted indole derivatives as histamine H3 antagonistsReactant for preparation of potent and selective inhibitors of human reticulocyte 15-lipoxygenase-1Reactant for preparation of inhibitors of Gli1-mediated transcription in Hedgehog pathwayReactant for preparation of pyridinyl carboxylates as SARS-CoV 3CL proinhibitorsReactant for preparation of substituted bipiperidinylmethyl amides as CCR3 membrane binding ligandsReactant for preparation of indole amide hydroxamic acids as potent inhibitors of histone deacetylasesReactant for preparation of 2-[[[4′-chloro-[1,1-biphenyl]-4-yl]thio]methyl]-N-hydroxybutanamide derivatives as specific metalloproteinase

InChI:InChI=1/C9H7NO2/c11-9(12)7-2-1-3-8-6(7)4-5-10-8/h1-5,10H,(H,11,12)/p-1

Upstream product

• 39830-66-5 methyl 1H-indole-4-carboxylate 
• 52488-36-5 4-bromo-1H-indole 
• 2258-42-6 formyl acetic anhydride 
• 36892-19-0 (2-chloro-6-nitro-phenyl)-pyruvic acid 
• 24621-73-6 4-chloro-1H-indole-2-carboxylic acid 
• 83-42-1 6-chloro-2-nitrotoluene 
• 16136-52-0 4-cyanoindole 

Downstream Products

• 84401-11-6 benzyl indole-4-carboxylate 
• 1444-12-8 1-methyl-1H-indole-4-carboxylic acid methyl ester 
• 175647-03-7 2,3-dihydro-1H-indole-4-carboxylic acid 
• 208774-11-2 2,3-dihydro-indole-1,4-dicarboxylic acid 1-tert-butyl ester 
• 1035214-86-8 3-(3-chloro-4-isopropoxyphenyl)-5-(1H-indol-4-yl)-1,2,4-oxadiazole 
• 1153849-22-9 N-benzyl-1H-indole-4-carboxamide 
• 1238070-09-1 1-methyl-1H-benzoimidazole-2-carboxylic acid {(S)-3-[(1H-indole-4-carbonyl)-methyl-amino]-4-phenyl-butyl}-amide 
• 1238070-21-7 1H-indole-4-carboxylic acid {(S)-1-benzyl-3-[(pyridine-2-carbonyl)-amino]-propyl}-methyl-amide 
• 1034020-88-6 N-{2-[5-(diphenylmethyl)-2-oxo-1(2H)-pyridinyl]ethyl}-1H-indole-4-carboxamide 
• 1074-85-7 (1H-indol-4-yl)methanol 
• 1074-86-8 4-formyl indole 
• 84401-12-7 benzyl 1-benzoylindole-4-carboxylate 
• 84401-15-0 ethyl 1-benzoylindole-4-acetate 
• 84401-14-9 1-benzoyl-4-diazoacetylindole 

Relevant articles and documents

Indole- and benzothiophene-based histamine H3 antagonists

Previous research on histamine H3 antagonists has led to the development of a pharmacophore model consisting of a central phenyl core flanked by two alkylamine groups. Recent investigation of the replacement of the central phenyl core with heteroaromatic fragments resulted in the preparation of novel 3,5-, 3,6- and 3,7-substituted indole and 3,5-substituted benzothiophene analogs that demonstrate good to excellent hH3 affinities. Select analogs were profiled in a rat pharmacokinetic model.

Discovery of a Novel Class of Negative Allosteric Modulator of the Dopamine D2 Receptor Through Fragmentation of a Bitopic Ligand

Recently, we have demonstrated that N-((trans)-4-(2-(7-cyano-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)cyclohexyl)-1H-indole-2-carboxamide (SB269652) (1) adopts a bitopic pose at one protomer of a dopamine D2 receptor (D2R) dimer to negatively modulate the binding of dopamine at the other protomer. The 1H-indole-2-carboxamide moiety of 1 extends into a secondary pocket between the extracellular ends of TM2 and TM7 within the D2R protomer. To target this putative allosteric site, we generated and characterized fragments that include and extend from the 1H-indole-2-carboxamide moiety of 1. N-Isopropyl-1H-indole-2-carboxamide (3) displayed allosteric pharmacology and sensitivity to mutations of the same residues at the top of TM2 as was observed for 1. Using 3 as an "allosteric lead", we designed and synthesized an extensive fragment library to generate novel SAR and identify N-butyl-1H-indole-2-carboxamide (11d), which displayed both increased negative cooperativity and affinity for the D2R. These data illustrate that fragmentation of extended compounds can expose fragments with purely allosteric pharmacology.