304859-17-4

Basic information

• Product Name: 1-(3-CHLOROBENZYL)-5-OXOPYRROLIDINE-3-CARBOXYLICACID
• Synonyms: 1-(3-CHLOROBENZYL)-5-OXOPYRROLIDINE-3-CARBOXYLICACID
• CAS NO: 304859-17-4
• Molecular Formula: C₁₂H₁₂ClNO₃
• Molecular Weight: 253.68158
• Product Categories: Carboxylic Acids;Carboxylic Acids;Pyrrolidines
• Mol File: 304859-17-4.mol

Chemical Properties

• Melting Point: 148-149 °C(Solv: ethyl ether (60-29-7); methanol (67-56-1))
• Boiling Point: 496.9±45.0 °C(Predicted)
• Appearance: /
• Density: 1.418±0.06 g/cm3(Predicted)
• PKA: 4.48±0.20(Predicted)
• CAS DataBase Reference: 1-(3-CHLOROBENZYL)-5-OXOPYRROLIDINE-3-CARBOXYLICACID(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-CHLOROBENZYL)-5-OXOPYRROLIDINE-3-CARBOXYLICACID(304859-17-4)
• EPA Substance Registry System: 1-(3-CHLOROBENZYL)-5-OXOPYRROLIDINE-3-CARBOXYLICACID(304859-17-4)

Safety Data

• Statements: 43
• Safety Statements: 36/37
• HazardClass: IRRITANT
• Hazardous Substances Data: 304859-17-4(Hazardous Substances Data)

Usage

Family

Pyrrolidine-3-carboxylic acids

Use

Vasodilator and antiplatelet agent

Investigation

Potential therapeutic effects in cardiovascular and cerebrovascular diseases

Chemical Structure

Contains a pyrrolidine ring, chlorine-substituted benzyl group, and a carboxylic acid functional group

Preclinical Studies

Shown promise in inhibiting platelet aggregation and improving blood flow

Potential Applications

Therapeutic agent for cardiovascular conditions

Upstream product

• 97-65-4 2-methylenesuccinic acid 
• 4152-90-3 m-chlorobenzylamine 

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.

CYCLIC AMIDE COMPOUNDS, PROCESS FOR THE PREPARATION OF THE SAME AND USES THEREOF

A compound of the formula: wherein R1 is a hydrocarbon group, R2 is a hydrocarbon group having 2 or more carbon atoms, where R1 and R2 may in combination form, together with an adjacent nitrogen atom, a ring optionally having a substituent or substituents, R3 is a hydrocarbon group optionally having a substituent or substituents or a heterocyclic group optionally having a substituent or substituents, R4 is a hydrogen atom, a hydrocarbon group, a heterocyclic group and the like, E is a divalent chain hydrocarbon group and the like, G is CO or SO2, J is a nitrogen atom, a methine group and the like, and Q and R are each a divalent chain C1-3 hydrocarbon group and the like, and a salt thereof show a superior CCR5 antagonistic activity and are useful as agents for the prophylaxis or treatment of HIV infection of human peripheral blood mononuclear cells, particularly AIDS.