473797-79-4

Basic information

• Product Name: Benzoic acid, 3-[[(2S)-2-(1-pyrrolidinylcarbonyl)-1-pyrrolidinyl]carbonyl]-, methyl ester
• CAS NO: 473797-79-4
• Molecular Formula: C18H22N2O4
• Molecular Weight: 330.384
• Mol File: 473797-79-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 3-[[(2S)-2-(1-pyrrolidinylcarbonyl)-1-pyrrolidinyl]carbonyl]-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 3-[[(2S)-2-(1-pyrrolidinylcarbonyl)-1-pyrrolidinyl]carbonyl]-, methyl ester(473797-79-4)
• EPA Substance Registry System: Benzoic acid, 3-[[(2S)-2-(1-pyrrolidinylcarbonyl)-1-pyrrolidinyl]carbonyl]-, methyl ester(473797-79-4)

Safety Data

• Hazardous Substances Data: 473797-79-4(Hazardous Substances Data)

Upstream product

• 1877-71-0 benzene 1,3-dicarboxylic acid monomethyl ester 
• 1236267-58-5 L-prolyl-pyrrolidine hydrochloride 
• 144243-44-7 tert-butyl (S)-2-(pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylate 

Downstream Products

• 473797-91-0 isophthalic acid L-prolyl-2(S)-(acetoxyacetyl)pyrrolidine L-prolyl-pyrrolidine amide 
• 473797-89-6 isophthalic acid L-prolyl-pyrrolidine L-prolinol amide 
• 485834-26-2 4-((S)-1-{3-[(S)-2-(Pyrrolidine-1-carbonyl)-pyrrolidine-1-carbonyl]-benzoyl}-pyrrolidine-2-carbonyl)-piperazine-1-carboxylic acid tert-butyl ester 
• 473797-81-8 isophthalic acid L-proline L-prolyl-pyrrolidine amide 
• 473797-85-2 isophthalic acid (L-proline methyl ester) L-prolyl-pyrrolidine amide 
• 473797-83-0 isophthalic acid mono(L-prolyl-pyrrolidine) amide 

Relevant articles and documents

New prolyl oligopeptidase inhibitors developed from dicarboxylic acid bis(L-prolyl-pyrrolidine) amides

Isophthalic acid bis(L-prolyl-pyrrolidine) amide is a very potent prolyl oligopeptidase inhibitor, but it has a log P value of -0.2, which is very low for a compound targeted to the brain. Therefore, these types of compounds were further modified to improve the structure-activity relationships, with the focus on increasing the log P value. The inhibitory activity against prolyl oligopeptidase from pig brain was tested in vitro. The most promising compounds resulted from replacing the pyrrolidinyl group at the P5 site by cycloalkyl groups, such as cyclopentyl and cyclohexyl groups, and by a phenyl group. These compounds are slightly more potent, and they have a significantly higher log P value. The potency of these compounds was further increased by replacing the pyrrolidinyl group at the P1 site by 2(S)-cyanopyrrolidinyl and 2(S)-(hydroxyacetyl)pyrrolidinyl groups.