121332-92-1

Basic information

• Product Name: 7-((2S,4S)-4-Acetylamino-2-methyl-pyrrolidin-1-yl)-6-fluoro-1-(4-fluoro-phenyl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester
• Synonyms: 7-((2S,4S)-4-Acetylamino-2-methyl-pyrrolidin-1-yl)-6-fluoro-1-(4-fluoro-phenyl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester
• CAS NO: 121332-92-1
• Molecular Weight: 470.476
• Mol File: 121332-92-1.mol

Chemical Properties

• CAS DataBase Reference: 7-((2S,4S)-4-Acetylamino-2-methyl-pyrrolidin-1-yl)-6-fluoro-1-(4-fluoro-phenyl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 7-((2S,4S)-4-Acetylamino-2-methyl-pyrrolidin-1-yl)-6-fluoro-1-(4-fluoro-phenyl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester(121332-92-1)
• EPA Substance Registry System: 7-((2S,4S)-4-Acetylamino-2-methyl-pyrrolidin-1-yl)-6-fluoro-1-(4-fluoro-phenyl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester(121332-92-1)

Safety Data

• Hazardous Substances Data: 121332-92-1(Hazardous Substances Data)

Upstream product

• 2584-71-6 cis-hydroxy-D-proline 
• 114676-60-7 (2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methanesulfonyloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 114760-51-9 (2R,4R)-1-(tert-butixycarbonyl)-4-<(tert-butyldimethylsilyl)oxy>-2-carbomethoxypyrrolidine 
• 114676-58-3 (2R,4R)-tert-butyl 4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate 
• 114676-61-8 tert-butyl (2S,4R)-4-hydroxyl-2-methylpyrrolidine-1-carboxylate 
• 114677-04-2 (2S,4R)-4-Methanesulfonyloxy-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 213699-41-3 tert-butyl (2S,4R)-4-((tert-butyldimethylsilyl)oxy)-2-methylpyrrolidine-1-carboxylate 
• 152673-32-0 (2S,4S)-4-amino-2-methylpyrrolidine-1-carboxylic acid tert-butyl ester 
• 113451-51-7 (2S,4S)-4-azido-1-(tert-butoxycarbonyl)-2-methylpyrrolidine 
• 113451-55-1 (2S,4S)-4-acetamido-1-(tert-butoxycarbonyl)-2-methylpyrrolidine 
• 114676-59-4 (2R,4R)-4-hydroxy-2-methoxycarbonylpyrrolidine hydrochloride 
• 114676-69-6 (2R,4R)-1-tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate 
• 100491-30-3 ethyl 7-chloro-1-(4-fluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate 
• 114677-00-8 (2S,4S)-4-Acetylamino-2-methylpyrrolidine 

Downstream Products

• 114676-87-8 (2'S,4'S)-7-(4'-amino-2'-methylpyrrolidinyl)-1,4-dihydro-6-fluoro-1-(p-fluorophenyl)-4-oxo-1,8-naphthyridine-3-carboxylic acid hydrochloride 

Relevant articles and documents

Design, Synthesis, and Properties of (4S)-7-(4-Amino-2-substituted-pyrrolidin-1-yl)quinolone-3-carboxylic Acids

The quinolinecarboxylic acids constitute a class of extremely potent and orally active broad-spectrum antibacterial agents.These compounds have been shown to inhibit DNA gyrase, a key enzyme in bacterial DNA replication.The 7-(3-aminopyrrolidinyl)quinolone A-60969 (1) is a particularly potent member of this class and is currently undergoing clinical evaluation.We have studied a series of enantiomerically homogeneous (4S)-7-(4-amino-2-substituted-pyrrolidinyl)quinolones in an effort to utilize the 2-position of the pyrrolidine moiety to improve upon the solubility and pharmacokinetic properties of this class of compounds while still maintaining potent antibacterial activity.We have found that the absolute stereochemistry at the 2-position of the pyrrolydine ring is critical to the maintenance of such activity.In this paper, we report the full details of the asymmetric synthesis and the in vitro and in vivo structure-activity relationships of this series of compounds as well as the physiochemical properties, such as water solubility and log P, associated with the structural modifications.We also discuss the pharmacokinetic properties of several of these compounds in mice and the pharmacokinetics of 59, which has the best overall properties of agents in this study, in dog.