114676-55-0

Basic information

• Product Name: D-Proline, 4-azido-1-(phenylmethyl)-, methyl ester, trans-
• CAS NO: 114676-55-0
• Molecular Formula: C13H16N4O2
• Molecular Weight: 260.296
• Mol File: 114676-55-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: D-Proline, 4-azido-1-(phenylmethyl)-, methyl ester, trans-(CAS DataBase Reference)
• NIST Chemistry Reference: D-Proline, 4-azido-1-(phenylmethyl)-, methyl ester, trans-(114676-55-0)
• EPA Substance Registry System: D-Proline, 4-azido-1-(phenylmethyl)-, methyl ester, trans-(114676-55-0)

Safety Data

• Hazardous Substances Data: 114676-55-0(Hazardous Substances Data)

Upstream product

• 77449-94-6 (2R,4R)-4-hydroxypyrrolidine-2-carboxylic acid hydrochloride 
• 51-35-4 4R-4-hydroxyproline 
• 100-44-7 benzyl chloride 
• 2584-71-6 cis-hydroxy-D-proline 
• 114676-59-4 (2R,4R)-4-hydroxy-2-methoxycarbonylpyrrolidine hydrochloride 
• 114676-53-8 (2R,4R)-methyl 1-benzyl-4-hydroxypyrrolidine-2-carboxylate 
• 114676-54-9 (2R,4R)-1-benzyl-2-carbomethoxy-4-<(methylsulfonyl)oxy>pyrrolidine 

Downstream Products

• 114676-80-1 (2'S,4'S)-7-<4'-amino-2'-(hydroxymethyl)pyrrolidinyl>-1-(2,4-difluorophenyl)-1,4-dihydro-6-fluoro-4-oxoquinoline-3-carboxylic acid 
• 114676-51-6 (2'R,4'S)-7-<4'-amino-2'-(hydroxymethyl)pyrrolidinyl>-1-(2,4-difluorophenyl)-1,4-dihydro-6-fluoro-4-oxoquinoline-3-carboxylic acid 
• 114677-03-1 7-((2R,4S)-4-Acetylamino-2-hydroxymethyl-pyrrolidin-1-yl)-1-(2,4-difluoro-phenyl)-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester 
• 114676-56-1 (2R,4S)-2-Acetoxymethyl-4-acetylamino-1-benzylpyrrolidine 

Relevant articles and documents

A sub-milligram-synthesis protocol for in vitro screening of HDAC11 inhibitors

This work demonstrated the high efficiency of a sub-milligram-synthesis based medicinal chemistry method. Totally 72 compounds, consisting a tri-substituted pyrrolidine core, were prepared. Around 0.1 mg of each compound was solid-phase synthesized. Based on the additive property of UV absorptions of unconjugated chromophores of a molecule, these compounds were quantified by UV measurement. A hit, whose IC50 value was 1.2 μM in HDAC11 inhibition assays, highlights the applicability of the approach reported here in future optimization works.

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.