173908-58-2

Basic information

• Product Name: ethyl 1-{[5-chloro-2-(propanoylamino)phenyl]sulfonyl}-1H-pyrrole-2-carboxylate
• Synonyms: 1H-pyrrole-2-carboxylic acid, 1-[[5-chloro-2-[(1-oxopropyl)amino]phenyl]sulfonyl]-, ethyl ester
• CAS NO: 173908-58-2
• Molecular Formula: C₁₆H₁₇ClN₂O₅S
• Molecular Weight: 384.8346
• Mol File: 173908-58-2.mol
• Article Data: 2

Chemical Properties

• Density: 1.38g/cm³
• Refractive Index: 1.602
• PKA: 12.74±0.70(Predicted)
• CAS DataBase Reference: ethyl 1-{[5-chloro-2-(propanoylamino)phenyl]sulfonyl}-1H-pyrrole-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 1-{[5-chloro-2-(propanoylamino)phenyl]sulfonyl}-1H-pyrrole-2-carboxylate(173908-58-2)
• EPA Substance Registry System: ethyl 1-{[5-chloro-2-(propanoylamino)phenyl]sulfonyl}-1H-pyrrole-2-carboxylate(173908-58-2)

Safety Data

• Hazardous Substances Data: 173908-58-2(Hazardous Substances Data)

Upstream product

• 79-03-8 propionyl chloride 
• 180905-84-4 1-[(2-amino-5-chlorophenyl)sulfonyl]-2-ethoxycarbonyl-1H-pyrrole 

Relevant articles and documents

Anti-HIV-1 NNRT agents: Acylamino Pyrryl Aryl Sulfones (APASs) as truncated analogues of tricyclic PBTDs

Pyrryl Aryl Sulfones (PASs) bearing acylamino moieties at position 2 of the benzene ring were designed as truncated analogs of pyrrolo[1,2-b][1,2,5]benzothiadiazepine 5,5-dioxides (PBTDs). Acylamino-PASs (APASs) were synthesized by reacting 1-(2-amino-5-chlorobenzenesulfonyl)-2-ethoxycarbonyl-1H-pyrrole with alkanoyl, aroyl or benzenesulfonyl halides in the presence of pyridine or sodium hydrogen carbonate. Some of test compounds were achieved by treating 1-(2-bromoacetylamino-5-chlorobenzenesulfonyl)-2-ethoxycarbonyl-1H-pyrrole with appropriate amines, heterocycles or sodium thiomethoxide. Reaction of 1-(2-acetylamino-5-chlorobenzenesulfonyl)-1H-pyrrole with acetyl chloride in the presence of boron trifluoride ethyl etherate or aluminum chloride afforded the related 2- and 3-acetyl-1H-pyrrole isomers. The most potent derivatives 1- [2-(1-X-acetyl)amino-5-chlorobenzenesulfonyl]-2-ethoxycarbonyl-1H-pyrroles (X = CH3O, CH3S) were active at submicromolar concentrations, comparable with that of nevirapine. Various derivatives were as active as the related cyclic pyrrolobenzothiadiazepines (PBTDs). A binding mode investigation by molecular modeling and docking studies is reported for these novel NNRTIs. Furthermore, some information about the relation between hydrophobicity and anti-HIV activity were evaluated using calculated logP values.