605665-80-3

Basic information

• Product Name: (2S)-2-((4-fluorophenyl)sulfonylamino)-3-methyl-N-((3S)-tetrahydro-2-oxo-3-furanyl)butanamide
• Synonyms: (2S)-2-((4-fluorophenyl)sulfonylamino)-3-methyl-N-((3S)-tetrahydro-2-oxo-3-furanyl)butanamide
• CAS NO: 605665-80-3
• Molecular Weight: 358.391
• Mol File: 605665-80-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2S)-2-((4-fluorophenyl)sulfonylamino)-3-methyl-N-((3S)-tetrahydro-2-oxo-3-furanyl)butanamide(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-2-((4-fluorophenyl)sulfonylamino)-3-methyl-N-((3S)-tetrahydro-2-oxo-3-furanyl)butanamide(605665-80-3)
• EPA Substance Registry System: (2S)-2-((4-fluorophenyl)sulfonylamino)-3-methyl-N-((3S)-tetrahydro-2-oxo-3-furanyl)butanamide(605665-80-3)

Safety Data

• Hazardous Substances Data: 605665-80-3(Hazardous Substances Data)

Upstream product

• 2185-03-7 L-homoserine lactone hydrochloride 
• 190275-58-2 N-((4-fluorophenyl)sulfonyl)-L-valine N-hydroxysuccinimide ester 
• 72-18-4 L-valine 
• 349-88-2 4-Fluorobenzenesulfonyl chloride 
• 97801-48-4 (S)-2-(4-fluorobenzenesulfonylamino)-3-methylbutanoic acid 

Relevant articles and documents

Exploration of cornea permeable calpain inhibitors as anticataract agents

To explore cornea permeable calpain inhibitors, four compounds displaying different characteristics were designed and synthesized based on the known potent calpain inhibitor, peptidyl aldehyde SJA6017. Two approaches were adopted; an improvement in the physicochemical properties, and conversion of the active aldehyde. The water-soluble peptidyl aldehyde 1 containing a pyridine ring at the P3 site showed a modest inhibition against calpains and an improvement of corneal permeability in comparison with SJA6017. Replacement of the aldehyde of SJA6017 by an α-ketoamide provided compound 2 that was approximately equipotent with SJA6017, but it was extremely water-insoluble. However, compound 3, in which the aldehyde was converted into a cyclic hemiacetal, proved to be a less potent calpain inhibitor than SJA6017, but demonstrated excellent transcorneal permeability. Further modification generating the cyclic hemiacetal 4 containing a thiourea linker between the P3 and P2 sites exhibited potent inhibitory activities, high cornea permeability and excellent efficacy in the rat lens culture cataract model.