304858-62-6

Basic information

• Product Name: N-(2-hydroxyethyl)-1-methyl-5-oxo-N-phenylpyrrolidine-3-carboxamide
• Synonyms: N-(2-hydroxyethyl)-1-methyl-5-oxo-N-phenylpyrrolidine-3-carboxamide
• CAS NO: 304858-62-6
• Molecular Weight: 262.309
• Mol File: 304858-62-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: N-(2-hydroxyethyl)-1-methyl-5-oxo-N-phenylpyrrolidine-3-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-hydroxyethyl)-1-methyl-5-oxo-N-phenylpyrrolidine-3-carboxamide(304858-62-6)
• EPA Substance Registry System: N-(2-hydroxyethyl)-1-methyl-5-oxo-N-phenylpyrrolidine-3-carboxamide(304858-62-6)

Safety Data

• Hazardous Substances Data: 304858-62-6(Hazardous Substances Data)

Upstream product

• 679003-56-6 ethyl 2-{[(1-methyl-5-oxopyrrolidin-3-yl)carbonyl]-anilino}acetate 
• 679003-57-7 2-{[(1-methyl-5-oxopyrrolidin-3-yl)carbonyl]-anilino}acetic acid 
• 304858-50-2 1-methyl-5-oxo-N-phenylpyrrolidine-3-carboxamide 
• 97-65-4 2-methylenesuccinic acid 
• 42346-68-9 1-Methyl-5-oxo-3-pyrrolidinecarboxylic Acid 

Downstream Products

• 304858-63-7 N-(2-chloroethyl)-N-phenyl-1-methyl-5-oxo-3-pyrrolidinecarboxamide 

Relevant articles and documents

CCR5 antagonists as anti-HIV-1 agents. 1. Synthesis and biological evaluation of 5-oxopyrrolidine-3-carboxamide derivatives

A novel lead compound, N-{3-[4-(4-fluorobenzoyl)piperidin-1-yl]propyl}-1- methyl-5-oxo-N-phenylpyrrolidine-3-carboxamide (1), was identified as a CCR5 antagonist by high-throughput screening using [125I]RANTES and CCR5-expressing CHO cells. The IC50 value of 1 was 1.9 μM. In an effort to improve the binding affinity of 1, a series of 5-oxopyrrolidine-3- carboxamides was synthesized. Introduction of 3,4-dichloro substituents to the central phenyl ring (10i, IC50=0.057 μM; 11b, IC 50=0.050 μM) or replacing the 1-methyl group of the 5-oxopyrrolidine moiety with a 1-benzyl group (12e, IC50=0.038 μM) was found to be effective for improving CCR5 affinity. Compound 10i, 11b, and 12e also inhibited CCR5-using HIV-1 envelope-mediated membrane fusion with IC50 values of 0.44, 0.19, and 0.49 μM, respectively.