155091-74-0

Basic information

• Product Name: 1H-Imidazole-2-methanol, 5-butyl-1-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-
• CAS NO: 155091-74-0
• Molecular Formula: C22H24N6O
• Molecular Weight: 388.472
• Mol File: 155091-74-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1H-Imidazole-2-methanol, 5-butyl-1-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Imidazole-2-methanol, 5-butyl-1-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-(155091-74-0)
• EPA Substance Registry System: 1H-Imidazole-2-methanol, 5-butyl-1-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-(155091-74-0)

Safety Data

• Hazardous Substances Data: 155091-74-0(Hazardous Substances Data)

Usage

Imidazole ring

The compound has an imidazole ring, which is a five-membered ring with one nitrogen atom and two hydrogen atoms.

Methanol group

The imidazole ring is attached to a methanol group (-OH), which can form hydrogen bonds and participate in other polar interactions.

Butyl chain

The compound has a butyl chain (-CH2-CH2-CH2-CH3) attached to the imidazole ring, which can increase the compound's lipophilicity and membrane permeability.

Biphenyl group

The compound contains a biphenyl group (-C6H5-C6H5), which can contribute to the compound's hydrophobicity and may interact with hydrophobic pockets in proteins.

Tetrazol-5-yl substituent

The compound has a tetrazol-5-yl substituent (-N4H4) attached to the biphenyl group, which can act as a hydrogen bond acceptor and may contribute to the compound's binding affinity to biological targets.

Biological and pharmaceutical applications

The compound has potential biological and pharmaceutical applications due to its unique structure and ability to interact with biological systems such as enzymes or receptors. The specific properties and functions of this compound are yet to be fully understood.

Upstream product

• 155091-95-5 5-butyl-2-hydroxymethyl-1-<<2'-<(N-triphenylmethyl)tetrazol-5-yl>biphenyl-4-yl>methyl>imidazole 
• 1400933-88-1 5-butyl-2-hydroxymethyl-1-[[(2'-(2-trityl)-2H-tetrazol-5-yl)biphenyl-4-yl]methyl]-3-[(2-(trimethylsilyl)ethoxy)methyl]-1H-imidazolium bromide 
• 1400933-86-9 5-butyl-1-[[(2'-(2-trityl)-tetrazol-5-yl)biphenyl-4-yl]methyl]-3-[(2-(trimethylsilyl)ethoxy)methyl]-1H-imidazolium bromide 
• 1400933-84-7 4-butyl-2-hydroxymethyl-1-[(2-(trimethylsilyl)ethoxy)methyl]-1H-imidazole 
• 133051-88-4 N-(triphenylmethyl)-5-<4'-(bromomethyl)biphenyl-2-yl>tetrazole 
• 133909-97-4 N-(trityl)-5-[4?-(methyl)biphenyl-2-yl]-2H-tetrazole 
• 114772-53-1 2-Cyano-4'-methylbiphenyl 
• 214360-47-1 2-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-benzonitrile 
• 146953-86-8 4-n-Butyl-imidazole 
• 120568-11-8 5-<4'-Methyl-1,1'-biphenyl-2-yl>-1H-tetrazole 

Relevant articles and documents

The discovery of new potent non-peptide Angiotensin II AT1 receptor blockers: A concise synthesis, molecular docking studies and biological evaluation of N-substituted 5-butylimidazole derivatives

A convenient and facile synthesis, in silico docking studies and in vitro biological evaluation of N-substituted 5-butylimidazole derivatives as potent Angiotensin II (ANG II) receptor type 1 (AT1) blockers (ARBs) has been reported in the current study. Our efforts have been directed towards the development of an efficient synthetic route allowing the facile introduction of substituents on the imidazole ring. In particular, a series of imidazole based compounds bearing the biphenyl moiety at the N - 1 position, a halogen atom at the C-4 and polar substituents such as hydroxymethyl, aldo or carboxy group at the C-2 position were designed and synthesized. These compounds were evaluated for binding to human AT1 receptor and for ANG II antagonism in vitro on isolated rat uterus. Among them, 5-butyl-1-[[2′-(2H-tetrazol-5-yl)biphenyl-4-yl] methyl]imidazole-2-carboxylic acid (30) exhibited higher binding affinity compared to the other analogues tested (-log IC50 = 8.46). The latter analogue was also found to be the most active in the rat uterotonic test (pA2 = 7.83). Importantly, the binding affinity was higher to that of losartan (-log IC50 = 8.25) indicating the importance of carboxy group at the C-2 position. Experimental findings are in good agreement with docking studies, which were undertaken in order to investigate ligand/AT1 receptor interactions.