221382-11-2

Basic information

• Product Name: Benzoic acid, 3-[(1-ethylpropyl)amino]-4-(2-oxo-1-pyrrolidinyl)-, methyl ester
• CAS NO: 221382-11-2
• Molecular Formula: C17H24N2O3
• Molecular Weight: 304.389
• Mol File: 221382-11-2.mol

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 3-[(1-ethylpropyl)amino]-4-(2-oxo-1-pyrrolidinyl)-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 3-[(1-ethylpropyl)amino]-4-(2-oxo-1-pyrrolidinyl)-, methyl ester(221382-11-2)
• EPA Substance Registry System: Benzoic acid, 3-[(1-ethylpropyl)amino]-4-(2-oxo-1-pyrrolidinyl)-, methyl ester(221382-11-2)

Safety Data

• Hazardous Substances Data: 221382-11-2(Hazardous Substances Data)

Upstream product

• 36151-44-7 4-(2-oxopyrrolidin-1-yl)benzoic acid 
• 96-22-0 pentan-3-one 
• 221381-91-5 1-(4-methoxycarbonyl-2-aminophenyl)pyrrolidin-2-one 
• 234110-57-7 1-{2-{[(Amino)(imino)methyl]amino}-4-carboxyphenyl}pyrrolidin-2-one 
• 221381-90-4 1-(4-methoxycarbonyl-2-nitrophenyl)pyrrolidin-2-one 
• 221381-89-1 1-(4-methoxycarbonylphenyl)pyrrolidin-2-one 
• 150-13-0 4-amino-benzoic acid 

Relevant articles and documents

Pyrrolidin-2-one compounds and their use as neuraminidase inhibitors

A compound having the formula: wherein all variables are as defined in the specification, for use as a neuramninidase inhibitor.

Potent inhibition of influenza sialidase by a benzoic acid containing a 2-pyrrolidinone substituent

On the basis of the lead compound 4-(N-acetylamino)-3-guanidinobenzoic acid (BANA 113), which inhibits influenza A sialidase with a K(i) of 2.5 μM, several novel aromatic inhibitors of influenza sialidases were designed. In this study the N-acetyl group of BANA 113 was replaced with a 2- pyrrolidinone ring, which was designed in part to offer opportunities for introduction of spatially directed side chains that could potentially interact with the 4-, 5-, and/or 6-subsites of sialidase. While the parent structure 1-(4-carboxy-2-guanidinophenyl)pyrrolidin-2-one (8) was only a modest inhibitor of sialidase, the introduction of a hydroxymethyl or bis(hydroxymethyl) substituent at the C5' position of the 2-pyrrolidinone ring resulted in inhibitors (9 and 12, respectively) with low micromolar activity. Crystal structures of these inhibitors in complex with sialidase demonstrated that the substituents at the 5'-position of the 2-pyrrolidinone ring interact in the 4- and/or 5-subsites of the enzyme. Replacement of the guanidine in 12 with a hydrophobic 3-pentylamino group resulted in a large enhancement in binding to produce an inhibitor (14) with an IC50 of about 50 nM against influenza A sialidase, although the inhibition of influenza B sialidase was 2000-fold less. This represents the first reported example of a simple, achiral benzoic acid with potent (low nanomolar) activity as an inhibitor of influenza sialidase.