851889-24-2

Upstream product

• 60639-52-3 N²-methylbenzene-1,2,3-triamine 
• 5910-19-0 N-methyl-2,6-dinitroaniline 
• 606-21-3 1-chloro-2,6-dinitrobenzene 
• 851886-92-5 7-amino-1-methyl-1,3-dihydro-2H-benzimidazol-2-one 
• 851889-26-4 4-[(1-methyl-2-oxo-1,3-dihydro-2H-benzimidazol-7-yl)amino]benzonitrile 

Downstream Products

• 851889-27-5 4-[(2-chloro-1-methyl-1H-benzimidazol-7-yl)(1-methylethyl)amino]benzonitrile 

Relevant academic research and scientific papers

Discovery of a 7-arylaminobenzimidazole series as novel CRF1receptor antagonists

A promising lead compound 1 of a benzimidazole series has been identified as a corticotropin-releasing factor 1 (CRF1) receptor antagonist. In this study, we focused on replacement of a 7-alkylamino group of 1, predicted to occupy a large lipophilic pocket of a CRF1receptor, with an aryl group. During the course of this examination, we established new synthetic approaches to 2,7-diarylaminobenzimidazoles. The novel synthesis of 7-arylaminobenzimidazoles culminated in the identification of compounds exhibiting inhibitory activities comparable to the alkyl analog 1. A representative compound, p-methoxyanilino analog 16g, showed potent CRF binding inhibitory activity against a human CRF1receptor and human CRF1receptor antagonistic activity (IC50?=?27?nM, 56?nM, respectively). This compound exhibited ex vivo125I-Tyr0(125I-CRF) binding inhibitory activity in mouse frontal cortex, olfactory bulb, and pituitary gland at 20?mg/kg after oral administration. In this report, we discuss the structure–activity-relationship of these 7-arylamino-1H-benzimidazoles and their synthetic method.

NITROGEN-CONTAINING FUSED HETEROCYCLIC COMPOUNDS

There is provided a CRF receptor antagonist comprising a compound of the formula (I): wherein, ring A is a 5-membered ring represented by the formula (A'): wherein X is a carbon and X is an oxygen, a sulfur or - NR -,or formula (A"): wherein X is a nitrogen and R is an optionally substituted hydrocarbyl, Ris an amino substituted by two optionally substituted hydrocarbyl groups, Ris an phenyl, Y is CR or a nitrogen, Y is CRor a nitrogen and Yis CRor a nitrogen, provided that one or less of Y, Y, and Y is nitrogen, W is a bond, -(CH2)n-, and Z is a bond, -NR -,etc.; or a salt thereof or a prodrug thereof.