355823-54-0

Basic information

• Product Name: 7-Chloro-6-[({4-[(dipropylamino)sulphonyl]benzoyl}amino)sulphonyl]-2-oxo-1,2-dihydro-3-quinolylphosphonic Acid Diethyl Ester
• Synonyms: 7-Chloro-6-[({4-[(dipropylamino)sulphonyl]benzoyl}amino)sulphonyl]-2-oxo-1,2-dihydro-3-quinolylphosphonic Acid Diethyl Ester
• CAS NO: 355823-54-0
• Molecular Weight: 662.121
• Mol File: 355823-54-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 7-Chloro-6-[({4-[(dipropylamino)sulphonyl]benzoyl}amino)sulphonyl]-2-oxo-1,2-dihydro-3-quinolylphosphonic Acid Diethyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Chloro-6-[({4-[(dipropylamino)sulphonyl]benzoyl}amino)sulphonyl]-2-oxo-1,2-dihydro-3-quinolylphosphonic Acid Diethyl Ester(355823-54-0)
• EPA Substance Registry System: 7-Chloro-6-[({4-[(dipropylamino)sulphonyl]benzoyl}amino)sulphonyl]-2-oxo-1,2-dihydro-3-quinolylphosphonic Acid Diethyl Ester(355823-54-0)

Safety Data

• Hazardous Substances Data: 355823-54-0(Hazardous Substances Data)

Upstream product

• 355408-09-2 diethyl 7-chloro-6-(chlorosulfonyl)-2-oxo-1,2-dihydroquinolin-3-ylphosphonate 
• 355399-63-2 (7-Chloro-6-nitro-2-oxo-1,2-dihydro-3-quinolyl)phosphonic acid diethyl ester 
• 355399-64-3 (6-Amino-7-chloro-2-oxo-1,2-dihydro-3-quinolyl)phosphonic acid diethyl ester 
• 57-66-9 4-[(dipropylamino)sulfonyl]benzoic acid 
• 59236-37-2 2-amino-4-chlorobenzaldehyde 
• 34170-81-5 diethyl (2-chloro-2-oxoethyl)phosphonate 
• 355408-10-5 6-(Aminosulphonyl)-7-chloro-2-oxo-1,2-dihydro-3-quinolylphosphonic Acid Diethyl Ester 
• 355399-62-1 (7-Chloro-2-oxo-1,2-dihydro-3-quinolyl)phosphonic acid diethyl ester 
• 530083-91-1 [(5-Chloro-2-formyl-phenylcarbamoyl)methyl] phosphonic Acid Diethyl Ester 

Relevant articles and documents

Novel quinolinone-phosphonic acid AMPA antagonists devoid of nephrotoxicity.

We reported previously the synthesis and structure-activity relationships (SAR) in a series of 2-(1H)-oxoquinolines bearing different acidic functions in the 3-position. Exploiting these SAR, we were able to identify 6,7-dichloro-2-(1H)-oxoquinoline-3-phosphonic acid compound 3 (S 17625) as a potent, in vivo active AMPA antagonist. Unfortunately, during the course of the development, nephrotoxicity was manifest at therapeutically effective doses. Considering that some similitude exists between S 17625 and probenecid, a compound known to protect against the nephrotoxicity and/or slow the clearance of different drugs, we decided to synthesise some new analogues of S 17625 incorporating some of the salient features of probenecid. Replacement of the chlorine in position 6 by a sulfonylamine led to very potent AMPA antagonists endowed with good in vivo activity and lacking nephrotoxicity potential. Amongst the compounds evaluated, derivatives 7a and 7s appear to be the most promising and are currently evaluated in therapeutically relevant stroke models.