58973-41-4

Basic information

• Product Name: β-Phenylhydrocinnamic acid hydrazide
• Synonyms: β-Phenylhydrocinnamic acid hydrazide;2-09-00-00474 (Beilstein Handbook Reference);3,3-di(phenyl)propanehydrazide;3,3-di(phenyl)propionohydrazide;Benzenepropanoic acid, beta-phenyl-, hydrazide;beta-Phenylhydrocinnamic acid hydrazide;BRN 3305630;Hydrocinnamic acid, beta-phenyl-, hydrazide
• CAS NO: 58973-41-4
• Molecular Formula: C₁₅H₁₆N₂O
• Molecular Weight: 240.30034
• Mol File: 58973-41-4.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 462.6°C at 760 mmHg
• Flash Point: 233.6°C
• Appearance: /
• Density: 1.132g/cm³
• Vapor Pressure: 9.75E-09mmHg at 25°C
• Refractive Index: 1.593
• CAS DataBase Reference: β-Phenylhydrocinnamic acid hydrazide(CAS DataBase Reference)
• NIST Chemistry Reference: β-Phenylhydrocinnamic acid hydrazide(58973-41-4)
• EPA Substance Registry System: β-Phenylhydrocinnamic acid hydrazide(58973-41-4)

Safety Data

• Hazardous Substances Data: 58973-41-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H16N2O/c16-17-15(18)11-14(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,14H,11,16H2,(H,17,18)

Upstream product

• 7476-18-8 3,3-diphenyl-propionic acid ethyl ester 

Downstream Products

• 40691-62-1 (2,2-diphenyl-ethyl)-carbamic acid ethyl ester 

Relevant articles and documents

4-Alkyl-1,2,4-triazole-3-thione analogues as metallo-β-lactamase inhibitors

In Gram-negative bacteria, the major mechanism of resistance to β-lactam antibiotics is the production of one or several β-lactamases (BLs), including the highly worrying carbapenemases. Whereas inhibitors of these enzymes were recently marketed, they only target serine-carbapenemases (e.g. KPC-type), and no clinically useful inhibitor is available yet to neutralize the class of metallo-β-lactamases (MBLs). We are developing compounds based on the 1,2,4-triazole-3-thione scaffold, which binds to the di-zinc catalytic site of MBLs in an original fashion, and we previously reported its promising potential to yield broad-spectrum inhibitors. However, up to now only moderate antibiotic potentiation could be observed in microbiological assays and further exploration was needed to improve outer membrane penetration. Here, we synthesized and characterized a series of compounds possessing a diversely functionalized alkyl chain at the 4-position of the heterocycle. We found that the presence of a carboxylic group at the extremity of an alkyl chain yielded potent inhibitors of VIM-type enzymes with Ki values in the μM to sub-μM range, and that this alkyl chain had to be longer or equal to a propyl chain. This result confirmed the importance of a carboxylic function on the 4-substituent of 1,2,4-triazole-3-thione heterocycle. As observed in previous series, active compounds also preferentially contained phenyl, 2-hydroxy-5-methoxyphenyl, naphth-2-yl or m-biphenyl at position 5. However, none efficiently inhibited NDM-1 or IMP-1. Microbiological study on VIM-2-producing E. coli strains and on VIM-1/VIM-4-producing multidrug-resistant K. pneumoniae clinical isolates gave promising results, suggesting that the 1,2,4-triazole-3-thione scaffold worth continuing exploration to further improve penetration. Finally, docking experiments were performed to study the binding mode of alkanoic analogues in the active site of VIM-2.