39167-76-5

Basic information

• Product Name: 1H-Indole-2-carboxamide, 1-methyl-N-phenyl-
• CAS NO: 39167-76-5
• Molecular Formula: C16H14N2O
• Molecular Weight: 250.3
• Mol File: 39167-76-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1H-Indole-2-carboxamide, 1-methyl-N-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole-2-carboxamide, 1-methyl-N-phenyl-(39167-76-5)
• EPA Substance Registry System: 1H-Indole-2-carboxamide, 1-methyl-N-phenyl-(39167-76-5)

Safety Data

• Hazardous Substances Data: 39167-76-5(Hazardous Substances Data)

Upstream product

• 16136-58-6 N-methyl-1H-indole-2-carboxylic acid 
• 103-71-9 phenyl isocyanate 
• 32387-21-6 1-methyl-3-indolecarboxylic acid 
• 103-72-0 phenyl isothiocyanate 
• 118618-61-4 1-methyl-1H-indole-2-carbonyl chloride 
• 62-53-3 aniline 
• 603-76-9 1-methylindole 

Downstream Products

• 82414-34-4 1-methyl-3-chloroindol-2-carboxanilide 
• 1232594-46-5 9-methyl-2,3,4-triphenyl-2H-pyrido[3,4-b]indol-1(9H)-one 

Relevant articles and documents

Palladium-Catalyzed Decarboxylative ortho -Amidation of Indole-3-carboxylic Acids with Isothiocyanates Using Carboxyl as a Deciduous Directing Group

Palladium-catalyzed ortho-amidation of indole-3-carboxylic acids with isothiocyanates by using the deciduous directing group nature of carboxyl functionality to afford indole-2-amides is demonstrated. Both C-H functionalization and decarboxylation took place in one pot, and hence, this carboxyl group served as a unique, deciduous (or traceless) directing group. This reaction offers a broad substrate scope as demonstrated for several other heterocyclic carboxylic acids like chromene-3-carboxylic acid, imidazo[1,2-a]pyridine-2-carboxylic acid, benzofuran-2-carboxylic acid, pyrrole-2-carboxylic acid, and thiophene-2-carboxylic acid. In the reaction using 2-naphthoic acid, of the two possible isomers, only one isomer of the amide was exclusively formed. The indole-2-amide product underwent palladium-catalyzed C-H functionalization to afford the diindole-fused 2-pyridones by combining two molecules of the indole moiety, with the elimination of an amide group from one of them, attached at the C3-position for the C-C/C-N bond formation. The structures of key products are confirmed by X-ray crystallography.

Synthesis, structure-activity relationships and molecular modeling studies of new indole inhibitors of monoamine oxidases A and B

New monoamine oxidase inhibitors were synthesized as indole analogues of a previously reported pyrrole series. Several compounds were potent MAO-A (12, 17, 19-22, 31, 36, and 37) or MAO-B (14, 20, 24, 38, 44, and 46) inhibitors, and had Ki values in the nanomolar concentration range. In particular, 22 (Ki = 0.00092 μM, and SI = 68,478) was exceptionally potent and selective as MAO-A inhibitor. In molecular modeling studies, compounds 22, 24, 44, and 46 positioned the indole ring into an aromatic cavity of MAO-A, and established π-π stacking interactions with Tyr407, Tyr444, and FAD cofactor. However, only compound 22 was able to form hydrogen bonds with FAD, a finding which was in accordance with its potent anti-MAO-A activity. Conversely, 22/MAOB complex was highly unstable during the MD simulation.