69808-76-0

Basic information

• Product Name: N-benzyl-1H-indole-2-carboxamide
• Synonyms: N-benzyl-1H-indole-2-carboxamide
• CAS NO: 69808-76-0
• Molecular Weight: 250.3
• Mol File: 69808-76-0.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: N-benzyl-1H-indole-2-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzyl-1H-indole-2-carboxamide(69808-76-0)
• EPA Substance Registry System: N-benzyl-1H-indole-2-carboxamide(69808-76-0)

Safety Data

• Hazardous Substances Data: 69808-76-0(Hazardous Substances Data)

Upstream product

• 69808-63-5 1-(indole-2-carbonyl)-1H-imidazole 
• 100-46-9 benzylamine 
• 1477-50-5 Indole-2-carboxylic acid 
• 58881-45-1 Indole-2-carbonyl chloride 
• 586959-21-9 1H-1,2,3-benzotriazol-1-yl(1H-indol-2-yl)methanone 

Downstream Products

• 149685-64-3 N-((1H-indol-2-yl)methyl)-1-phenylmethanamine 
• 1316845-35-8 2-benzyl-3-phenyl-4-iodo-5-(3,4-dimethoxyphenyl)-5,10-dihydroazepino[3,4-b]indol-1(2H)-one 
• 1316845-37-0 2-benzyl-3-(4-methylphenyl)-4-iodo-5-(4-ethoxyphenyl)-5,10-dihydroazepino[3,4-b]indol-1(2H)-one 
• 1316845-41-6 2-benzyl-3-cyclohex-1-enyl-4-iodo-5-(4-ethoxyphenyl)-5,10-dihydroazepino[3,4-b]indol-1(2H)-one 
• 1316845-39-2 2-benzyl-3-(4-methylphenyl)-4-iodo-5-(4-chlorophenyl)-5,10-dihydroazepino[3,4-b]indol-1(2H)-one 

Relevant articles and documents

Cu(OAc)2-Triggered Cascade Reaction of Malonate-Tethered Acyl Oximes with Indoles, Indole-2-alcohols, and Indole-2-carboxamides

A Cu(OAc)2-promoted cascade reaction of malonate-tetherd acyl oximes with indoles, indole-2-alcohols, or indole-2-carboxmides provides facile access to polysubstituted 3-pyrrolin-2-ones. The reaction features the generation of two adjacent elec

AMIDATION METHOD AND ESTERIFICATION METHOD USING SULFONIC ACID HALIDE

PROBLEM TO BE SOLVED: To provide a safe and economical method for rapidly synthesizing amides and esters in high yield. SOLUTION: There is provided a method for amidating an amine or a derivative thereof using a sulfonic acid halide, where a sulfonic acid halide is allowed to act as an activator on a carboxylic acid or a derivative thereof to synthesize an active ester, and the active ester is reacted with an amine or a derivative thereof as a nucleophile to amidate the amine or the derivative thereof to obtain a corresponding amide or a derivative thereof. In a similar manner, a sulfonic acid halide is allowed to act as an activator on a carboxylic acid or a derivative thereof to synthesize an active ester, and the active ester is reacted with an alcohol or a derivative thereof as a nucleophile to esterify the alcohol or the derivative thereof to obtain a corresponding ester or a derivative thereof. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2016,JPO&INPIT

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.