1082954-00-4

Basic information

• Product Name: (S)-5-guanidino-2-(2-((2Z,5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-4-oxo-2-(phenylimino)thiazolidin-3-yl)-3-(pyridin-4-yl)propanamido)pentanamide
• Synonyms: (S)-5-guanidino-2-(2-((2Z,5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-4-oxo-2-(phenylimino)thiazolidin-3-yl)-3-(pyridin-4-yl)propanamido)pentanamide
• CAS NO: 1082954-00-4
• Molecular Weight: 660.754
• Mol File: 1082954-00-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (S)-5-guanidino-2-(2-((2Z,5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-4-oxo-2-(phenylimino)thiazolidin-3-yl)-3-(pyridin-4-yl)propanamido)pentanamide(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-5-guanidino-2-(2-((2Z,5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-4-oxo-2-(phenylimino)thiazolidin-3-yl)-3-(pyridin-4-yl)propanamido)pentanamide(1082954-00-4)
• EPA Substance Registry System: (S)-5-guanidino-2-(2-((2Z,5Z)-5-(4-hydroxy-3,5-dimethoxybenzylidene)-4-oxo-2-(phenylimino)thiazolidin-3-yl)-3-(pyridin-4-yl)propanamido)pentanamide(1082954-00-4)

Safety Data

• Hazardous Substances Data: 1082954-00-4(Hazardous Substances Data)

Upstream product

• 103-72-0 phenyl isothiocyanate 
• 96-32-2 bromoacetic acid methyl ester 
• 169555-95-7 (S)-N-(9-fluorenylmethoxycarbonyl)-β-(4-pyridyl)alanine 
• 134-96-3 syringic aldehyde 
• 187618-60-6 Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine 

Relevant articles and documents

Substituted 2-Imino-5-arylidenethiazolidin-4-one Inhibitors of Bacterial Type III Secretion

Diverse species of pathogenic Gram-negative bacteria use secretion systems to export a variety of protein toxins and virulence factors that help establish and maintain infection. Disruption of such secretion systems is a potentially effective therapeutic strategy. We developed a high-throughput screen and identified a trisaryl substituted 2-imino-5-arylidenethiazolidin-4-one, compound 1, as an inhibitor of the type III secretion system. Expansion of this chemotype enabled us to define the essential pharmacophore for type III secretion inhibition by this structural class. A synthetic diversity set helped us identify N-3 as the most permissive locus and led to the design of a panel of novel N-3-dipeptide-modified congeners with improved activity and physiochemical properties. We now report on the synthesis of these compounds, including a novel solid phase approach to the rapid generation of the dipeptide-thiazolidinone hybrids, and their in vitro characterization as inhibitors of type III secretion in Salmonella enterica serovar Typhimurium.