1571-91-1

Basic information

• Product Name: 5-nitro-2-(m-tolyl)-1H-benzo[d]imidazole
• Synonyms: 5-nitro-2-(m-tolyl)-1H-benzo[d]imidazole
• CAS NO: 1571-91-1
• Molecular Weight: 253.26
• Mol File: 1571-91-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 5-nitro-2-(m-tolyl)-1H-benzo[d]imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-nitro-2-(m-tolyl)-1H-benzo[d]imidazole(1571-91-1)
• EPA Substance Registry System: 5-nitro-2-(m-tolyl)-1H-benzo[d]imidazole(1571-91-1)

Safety Data

• Hazardous Substances Data: 1571-91-1(Hazardous Substances Data)

Upstream product

• 99-56-9 4-Nitrophenylene-1,2-diamine 
• 620-23-5 m-tolyl aldehyde 
• 99-04-7 m-Toluic acid 

Downstream Products

• 1593834-45-7 N-(2-m-tolyl-1H-benzo[d]imidazol-6-yl)quinolin-4-amine 
• 1571-96-6 2-m-tolyl-1H-benzo[d]imidazol-5-amine 

Relevant articles and documents

Fragment-based lead discovery of a novel class of small molecule antagonists of neuropeptide B/W receptor subtype 1 (GPR7)

Here, we report the discovery of a new class of NPBWR1 antagonists identified from a fragment-based screen. Compound 1 (cAMP IC50 = 250 μM; LE = 0.29) emerged as an initial hit. Further optimization of 1 by SAR-by-catalogue and chemical modification produced 21a (cAMP IC50 = 30 nM; LE = 0.39) with a 6700-fold increase in potency from fragment 1. Somewhat surprisingly, Schild analysis of compound 21a suggested that in vitro inhibition of NPW-mediated effects on upon cAMP accumulation were saturable, and that compound 21a dose-dependently increased [125I]-hNPW23 dissociation rate constants from NPBWR1 in kinetic binding studies. Collectively, these data are inconsistent with a classic surmountable, orthosteric mechanism of inhibition. The benzimidazole inhibitors reported herein may therefore represent a mechanistically differentiated class of compounds with which to form a better appreciation of the pharmacology and physiological roles of this central neuropeptide system.

Discovery of quinazolin-4-amines bearing benzimidazole fragments as dual inhibitors of c-Met and VEGFR-2

Both c-Met and VEGFR-2 are important targets for the treatment of cancers. In this study, a series of N-(2-phenyl-1H-benzo[d]imidazol-5-yl)quinazolin-4- amine derivatives were designed and identified as dual c-Met and VEGFR-2 inhibitors. Among these compounds bearing quinazoline and benzimidazole fragments, compound 7j exhibited the most potent inhibitory activity against c-Met and VEGFR-2 with IC50 of 0.05 μM and 0.02 μM, respectively. It also showed the highest anticancer activity against the tested cancer cell lines with IC50 of 1.5 μM against MCF-7 and 8.7 μM against Hep-G2. Docking simulation supported the initial pharmacophoric hypothesis and suggested a common mode of interaction at the ATP-binding site of c-Met and VEGFR-2, which demonstrates that compound 7j is a potential agent for cancer therapy deserving further researching.