118786-28-0

Basic information

• Product Name: Benzenebutanoic acid, a-methylene-, phenylmethyl ester
• CAS NO: 118786-28-0
• Molecular Formula: C18H18O2
• Molecular Weight: 266.34
• Mol File: 118786-28-0.mol

Chemical Properties

• CAS DataBase Reference: Benzenebutanoic acid, a-methylene-, phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenebutanoic acid, a-methylene-, phenylmethyl ester(118786-28-0)
• EPA Substance Registry System: Benzenebutanoic acid, a-methylene-, phenylmethyl ester(118786-28-0)

Safety Data

• Hazardous Substances Data: 118786-28-0(Hazardous Substances Data)

Upstream product

• 128038-39-1 2-methylene-4-phenylbutanoic acid 
• 100-39-0 benzyl bromide 
• 6628-68-8 ethyl 2-(ethoxycarbonyl)-4-phenylbutanoate 
• 103-63-9 1-phenyl-2-bromoethane 
• 27356-87-2 ethyl 2-phenethylpropenoate 
• 100-51-6 benzyl alcohol 

Downstream Products

• 153642-81-0 benzyl 2-((methoxyphosphinyl)methyl)-4-phenylbutanoate 
• 153642-82-1 (+/-)-benzyl 2-((hydroxyphosphinyl)methyl)-4-phenylbutanoate 

Relevant articles and documents

Synthesis and Structural/Functional Characterization of Selective M14 Metallocarboxypeptidase Inhibitors Based on Phosphinic Pseudopeptide Scaffold: Implications on the Design of Specific Optical Probes

Metallocarboxypeptidases (MCPs) of the M14 family are Zn2+-dependent exoproteases present in almost every tissue or fluid in mammals. These enzymes perform a large variety of physiological functions and are involved in several pathologies, such as pancreatic diseases, inflammation, fibrinolysis, and cancer. Here, we describe the synthesis and functional/structural characterization of a series of reversible tight-binding phosphinic pseudopeptide inhibitors that show high specificity and potency toward these proteases. Characterization of their inhibitory potential against a large variety of MCPs, combined with high-resolution crystal structures of three selected candidates in complex with human carboxypeptidase A (CPA)1, allowed to decipher the structural determinants governing selectivity for type-A of the M14A MCP family. Further, the phosphinic pseudopeptide framework was exploited to generate an optical probe selectively targeting human CPAs. The phosphinic pseudopeptides presented here constitute the first example of chemical probes useful to selectively report on type-A MCPs activity in complex media.

Design and pharmacological activity of phosphinic acid based NAALADase inhibitors

A novel series of phosphinic acid based inhibitors of the neuropeptidase NAALADase are described in this work. This series of compounds is the most potent series of inhibitors of the enzyme described to date. In addition, we have shown that these compounds are protective in animal models of neurodegeneration. Compound 34 significantly prevented neurodegeneration in a middle cerebral artery occlusion model of cerebral ischemia. In addition, in the chronic constrictive model of neuropathic pain, compound 34 significantly attenuated the hypersensitivity observed with saline-treated animals. These data suggest that NAALADase inhibition may provide a new approach for the treatment of both neurodegenerative disorders and peripheral neuropathies.

SUBSTITUTED PHOSPHINIC ACID CONTAINING PEPTIDYL DERIVATIVES AS ANTIDEGENERATIVE AGENTS

Novel phosphinic acid-containing peptidyl compounds of formula I are found to be useful inhibitors of matrix metalloendoproteinase-mediated diseases including osteoarthritis, rheumatoid arthritis, septic arthritis, tumor invasion in certain cancers, perio