136285-23-9

Basic information

• Product Name: 4’-((2-propyl-1H-benzo[d]imidazol-1-yl)methyl)-[1,1'-biphenyl]-2-carbonitrile
• Synonyms: 4’-((2-propyl-1H-benzo[d]imidazol-1-yl)methyl)-[1,1'-biphenyl]-2-carbonitrile
• CAS NO: 136285-23-9
• Molecular Weight: 351.451
• Mol File: 136285-23-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4’-((2-propyl-1H-benzo[d]imidazol-1-yl)methyl)-[1,1'-biphenyl]-2-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 4’-((2-propyl-1H-benzo[d]imidazol-1-yl)methyl)-[1,1'-biphenyl]-2-carbonitrile(136285-23-9)
• EPA Substance Registry System: 4’-((2-propyl-1H-benzo[d]imidazol-1-yl)methyl)-[1,1'-biphenyl]-2-carbonitrile(136285-23-9)

Safety Data

• Hazardous Substances Data: 136285-23-9(Hazardous Substances Data)

Upstream product

• 95-54-5 1,2-diamino-benzene 
• 5465-29-2 2-propyl-1H-benzimidazole 
• 114772-54-2 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile 

Downstream Products

• 133141-63-6 4’-((2-propyl-1H-benzo[d]imidazol-1-yl)methyl)-[1,1’-biphenyl]-2-carboxylicacid 

Relevant articles and documents

Tackling resistance in chronic myeloid leukemia: Novel cell death modulators with improved efficacy

The development of resistance poses a serious problem in the therapy of cancer due to the necessity of a multiple-drug and unlimited treatment of affected patients. In chronic myeloid leukemia (CML), the introduction of imatinib has revolutionized the the

Characterization of new PPARγ agonists: Benzimidazole derivatives - Importance of positions 5 and 6, and computational studies on the binding mode

In this and previous studies we investigated the importance of partial structures of Telmisartan on PPARγ activation. The biphenyl-4-ylmethyl moiety at N1 and residues at C2 of the central benzimidazole were identified to be essential for receptor activation and potency of receptor binding. Now we focused our attention on positions 5 and 6 of the central benzimidazole and introduced bromine (3b-5/6, 3c), phenylcarbonyl (3d-5/6), hydroxy(phenyl)methyl (3g-5/6), hydroxymethyl (3h-5/6) and formyl (3i) groups. The selection of these moieties was inspired by the structure of Losartan and its metabolite EXP3179. In order to increase the hydrophobicity of the central part of the molecule, the benzimidazole was exchanged by a naphtho[2,3-d]imidazole (5). The compounds 3a-3i and 5 were tested in a differentiation assay using 3T3-L1 preadipocytes and a luciferase assay using COS-7 cells, transiently transfected with pGal4-hPPARγDEF, pGal5-TK-pGL3 and pRL-CMV, as established models for the assessment of cellular PPARγ activation. An enhanced effect on PPARγ activation could be observed if lipophilic moieties are introduced in these positions. 4′-[(2-Propyl-1H-naphtho[2,3-d]imidazol-1-yl)methyl]biphenyl-2- carboxylic acid (5) was identified as the most potent compound with an EC 50 of 0.26 μM and the profile of a full agonist. Together with compounds of the former structure-activity relationship study (position 2-substituted benzimidazole derivatives 4a-4j), the binding mode of Telmisartan and its derivatives have been analyzed in 3D pharmacophore-driven docking experiments.