955930-70-8

Basic information

• Product Name: 4-HYDROXY-2'-METHYL[1,1'-BIPHENYL]-3-CARBALDEHYDE
• Synonyms: 4-HYDROXY-2'-METHYL[1,1'-BIPHENYL]-3-CARBALDEHYDE;AKOS BAR-0953
• CAS NO: 955930-70-8
• Molecular Formula: C₁₄H₁₂O₂
• Molecular Weight: 212.24
• Mol File: 955930-70-8.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-HYDROXY-2'-METHYL[1,1'-BIPHENYL]-3-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXY-2'-METHYL[1,1'-BIPHENYL]-3-CARBALDEHYDE(955930-70-8)
• EPA Substance Registry System: 4-HYDROXY-2'-METHYL[1,1'-BIPHENYL]-3-CARBALDEHYDE(955930-70-8)

Safety Data

• Hazardous Substances Data: 955930-70-8(Hazardous Substances Data)

Upstream product

• 14472-14-1 4-bromo-3-methylphenol 
• 87199-16-4 3-Formylphenylboronic acid 

Downstream Products

• 1453861-72-7 2-(3-(4-((2'-methyl-4'-(3-(methylsulfonyl)propoxy)-[1,1'-biphenyl]-3-yl)methoxy)phenyl)oxetan-3-yl)acetic acid 
• 1453861-71-6 ethyl 2-(3-(4-((2'-methyl-4'-(3-(methylsulfonyl)propoxy)-[1,1'-biphenyl]-3-yl)methoxy)phenyl)oxetan-3-yl)acetate 

Relevant articles and documents

Design, synthesis and biological evaluation of novel FFA1/GPR40 agonists: New breakthrough in an old scaffold

Based on an old phenoxyacetic acid scaffold, CPU014 (compound 14) has been identified as a superior agonist by comprehensive exploration of structure-activity relationship. In vitro toxicity study suggested that CPU014 has lower risk of hepatotoxicity than TAK-875. During acute toxicity study (5–500 mg/kg), a favorable therapeutic window of CPU014 was observed by evaluation of plasma profiles and liver slices. Moreover, CPU014 promotes insulin secretion in a glucose-dependent manner, while no GLP-1 secretion has been enhanced. Other than good pharmacokinetic properties, CPU014 significantly improved glucose tolerance both in normal and diabetic models without the risk of hypoglycemia. These subversive findings provided a safer candidate CPU014, which is currently in preclinical study to assess its potential for the treatment of diabetes.

Design, synthesis, and evaluation of a series of novel phenylpropanoic acid derivatives agonists for the FFA1

Free fatty acid 1 (FFA1/GPR40) has attracted extensive attention as a novel target for the treatment of type 2 diabetes for its role in the enhancement of insulin secretion with glucose dependency. Aiming to develop novel potent FFA1 agonists, a new series of phenylpropionic acid derivatives were designed and synthesized on the basis of the modification of chemical cement of TAK-875, AMG-837, and LY2881835. Among them, most promising compounds 7, 14, and 15 were obtained with EC50 values of 82, 79, and 88?nM, exhibiting a powerful agonistic activity compared to TAK-875 (95.1?nM). During Oral glucose tolerance test in normal mice, compound 7, 14, and 15 had significant glucose-lowering effect at the dose of 50?mg/kg. Furthermore, compound 15 (50?mg/kg) also significantly improved in glucose tolerance in type 2 diabetic mice. Herein, we reported the discovery and optimization of a series of potent FFA1 agonists. The discovery supported further exploration surrounding this scaffold.

PHENYL ALKANOIC ACID DERIVATIVES AS GPR AGONISTS

The present invention relates to phenyl alkanoic acid derivatives (the compounds of Formula (I)); and their isotopic forms, stereoisomeric and tautomeric forms and mixtures thereof in all ratios, or pharmaceutically acceptable salts, pharmaceutically acceptable solvates, prodrugs, polymorphs, N-oxides, S-oxides or carboxylic acid isosteres thereof. The invention also relates to processes for the preparation of compounds of Formula (I) and pharmaceutical compositions comprising one or more of the compounds of Formula (I). The said compounds and the pharmaceutical composition function as GPR (G-protein coupled receptor) agonists, particularly as GPR40 agonists, and are useful in the treatment of diseases or conditions mediated by GPR40. The present invention further relates to a method of treatment of diseases or conditions mediated by GPR40comprising administering to a subject in need thereof a therapeutically effective amount of the compounds of Formula (I).