306271-99-8

Basic information

• Product Name: 4'-(BROMOMETHYL)-[1,1'-BIPHENYL]-4-CARBOXYLIC ACID METHYL ESTER
• Synonyms: 4'-(BROMOMETHYL)-[1,1'-BIPHENYL]-4-CARBOXYLIC ACID METHYL ESTER;methyl 4'-(bromomethyl)-[1,1'-biphenyl]-4-carboxylate
• CAS NO: 306271-99-8
• Molecular Formula: C₁₅H₁₃BrO₂
• Molecular Weight: 305.16652
• Mol File: 306271-99-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 403.5±38.0 °C(Predicted)
• Appearance: /
• Density: 1.374±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 4'-(BROMOMETHYL)-[1,1'-BIPHENYL]-4-CARBOXYLIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-(BROMOMETHYL)-[1,1'-BIPHENYL]-4-CARBOXYLIC ACID METHYL ESTER(306271-99-8)
• EPA Substance Registry System: 4'-(BROMOMETHYL)-[1,1'-BIPHENYL]-4-CARBOXYLIC ACID METHYL ESTER(306271-99-8)

Safety Data

• Hazardous Substances Data: 306271-99-8(Hazardous Substances Data)

Upstream product

• 31614-66-1 tributyl(p-tolyl)stannane 
• 619-44-3 methyl 4-iodobenzoate 
• 5720-05-8 4-methylphenylboronic acid 
• 720-73-0 4'-methyl-biphenyl-4-carboxylic acid 
• 586-76-5 4-Bromobenzoic acid 
• 49742-56-5 methyl 4-(4-tolyl)benzoate 

Downstream Products

• 1429046-03-6 C₂₆H₂₄N₂O₂S 

Relevant articles and documents

New telmisartan-derived PPARγ agonists: Impact of the 3D-binding mode on the pharmacological profile

In previous studies, the 4′-((2-propyl-1H-benzo[d]imidazol-1-yl)methyl)-[1,1′-biphenyl]-2-carboxylic acid was identified as pharmacophoric core for PPARγ activation. In this structure-activity relationship study the C2-alkyl chain was elongated and the 2-COOH group was changed to a carbamide/carbonitrile or shifted to the 3- or 4-position. Furthermore, the benzo[d]imidazole was exchanged by 2,3-dihydrobenzo[d]thiazole or 1H-indole. C2-propyl derivatives showed the profile of partial agonists, while elongation of the C2-chain to that of an n-heptyl group or a 4-COOH shift changed the pharmacological profile to that of a potent full agonist. This finding can be explained by binding to the LBD in different ligand conformations. Two anchoring points (Tyr473 and Arg288) exist in the LBD, which have to be contacted to achieve receptor activation. In a crystal violet chemosensitivity assay using COS-7?cells and LNCaP cells expressing PPARγ only the carbamide derivatives influenced the cell growth, independently on the presence of the PPARγ. Therefore, receptor mediated cytotoxicity can be excluded.

Correlation of anti-HIV activity with anion spacing in a series of cosalane analogues with extended polycarboxylate pharmacophores

Cosalane and its synthetic derivatives inhibit the binding of gp120 to CD4 as well as the fusion of the viral envelope with the cell membrane. The binding of the cosalanes to CD4 is proposed to involve ionic interactions of the negatively charged carboxylates of the ligands with positively charged arginine and lysine amino acid side chains of the protein. To investigate the effect of anion spacing on anti-HIV activity in the cosalane system, a series of cosalane tetracarboxylates was synthesized in which the two proximal and two distal carboxylates are separated by 6-12 atoms. Maximum activity was observed when the proximal and distal carboxylates are separated by 8 atoms. In a series of cosalane amino acid derivatives containing glutamic acid, glycine, aspartic acid, β-alanine, leucine, and phenylalanine residues, maximum activity was displayed by the di(glutamic acid) analogue. A hypothetical model has been devised for the binding of the cosalane di(glutamic acid) conjugate to CD4. In general, the compounds in this series are more potent against HIV-1RF in CEM-SS cells than they are vs HIV-1IIIB in MT-4 cells, and they are least potent vs HIV-2ROD in MT-4 cells.