119601-52-4

Basic information

• Product Name: benzyl (S)-2-[(4-methylpiperazine-1-carbonyl)amino]-3-phenylpropionate
• Synonyms: benzyl (S)-2-[(4-methylpiperazine-1-carbonyl)amino]-3-phenylpropionate
• CAS NO: 119601-52-4
• Molecular Weight: 381.475
• Mol File: 119601-52-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: benzyl (S)-2-[(4-methylpiperazine-1-carbonyl)amino]-3-phenylpropionate(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl (S)-2-[(4-methylpiperazine-1-carbonyl)amino]-3-phenylpropionate(119601-52-4)
• EPA Substance Registry System: benzyl (S)-2-[(4-methylpiperazine-1-carbonyl)amino]-3-phenylpropionate(119601-52-4)

Safety Data

• Hazardous Substances Data: 119601-52-4(Hazardous Substances Data)

Upstream product

• 109-01-3 1-methyl-piperazine 
• 119624-66-7 benzyl (2S)-2-isocyanato-3-phenylpropanoate 
• 55112-42-0 4-methylpiperazine-1-carbonyl chloride monohydrochloride 
• 2462-32-0 L-phenylalanine benzyl ester hydrochloride 

Downstream Products

• 233277-99-1 4-Methyl-piperazine-1-carboxylic acid [(S)-1-((E)-(S)-3-benzenesulfonyl-1-phenethyl-allylcarbamoyl)-2-phenyl-ethyl]-amide 
• 115766-11-5 N-[(4-methyl-1-piperazinyl)carbonyl]-L-phenylalanine 

Relevant articles and documents

Self-Masked Aldehyde Inhibitors: A Novel Strategy for Inhibiting Cysteine Proteases

Cysteine proteases comprise an important class of drug targets, especially for infectious diseases such as Chagas disease (cruzain) and COVID-19 (3CL protease, cathepsin L). Peptide aldehydes have proven to be potent inhibitors for all of these proteases. However, the intrinsic, high electrophilicity of the aldehyde group is associated with safety concerns and metabolic instability, limiting the use of aldehyde inhibitors as drugs. We have developed a novel class of self-masked aldehyde inhibitors (SMAIs) for cruzain, the major cysteine protease of the causative agent of Chagas disease - Trypanosoma cruzi. These SMAIs exerted potent, reversible inhibition of cruzain (Ki? = 18-350 nM) while apparently protecting the free aldehyde in cell-based assays. We synthesized prodrugs of the SMAIs that could potentially improve their pharmacokinetic properties. We also elucidated the kinetic and chemical mechanism of SMAIs and applied this strategy to the design of anti-SARS-CoV-2 inhibitors.

Potency and selectivity of P2/P3-modified inhibitors of cysteine proteases from trypanosomes

A systematic study of P2 and P3 substitution in a series of vinyl sulfone cysteine protease inhibitors is described. The introduction of a methyl substituent in the P2 phenylalanine aryl ring had a favorable effect on protease inhibition and conferred modest selectivity for rhodesain over cruzain. Rhodesain selectivity could be enhanced further by combining these P2 modifications with certain P3 amide substituents.

RENIN INHIBITOR PEPTIDE COMPOUNDS, A PROCESS FOR THE PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME

A compound of the formula: STR1 wherein R 1 is aryl optionally substituted with a substituent selected from the group consisting of halogen and halo(lower)alkyl; lower alkyl or cyclo(lower) alkyl; andR 2 is hydrogen or lower alkyl, or R. sup.1 and R 2 are taken together with the attached nitrogen atom to form a heterocyclic group optionally substituted with a substituent selected from the group consisting of lower alkyl and esterified carboxy, R 3 is hydrogen or lower alkyl, andR 4 is lower alkyl,and its pharmaceutically acceptable salt, a process for the preparation thereof and pharmaceutical composition comprising the same.