59999-67-6

Basic information

• Product Name: 4-Thiazolidinecarboxylic acid, 2-phenyl-, (2S,4R)-
• CAS NO: 59999-67-6
• Molecular Formula: C10H11NO2S
• Molecular Weight: 209.269
• Mol File: 59999-67-6.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 4-Thiazolidinecarboxylic acid, 2-phenyl-, (2S,4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Thiazolidinecarboxylic acid, 2-phenyl-, (2S,4R)-(59999-67-6)
• EPA Substance Registry System: 4-Thiazolidinecarboxylic acid, 2-phenyl-, (2S,4R)-(59999-67-6)

Safety Data

• Hazardous Substances Data: 59999-67-6(Hazardous Substances Data)

Upstream product

• 52-89-1 l-cysteine hydrochloride 
• 100-52-7 benzaldehyde 
• 52-90-4 L-Cysteine 
• 32443-99-5 D-cysteine hydrochloride 

Downstream Products

• 69739-28-2 (4R)-3-acetyl-2t-phenyl-thiazolidine-4r-carboxylic acid methyl ester 
• 69739-24-8 (2S,4R)-N-acetyl-2-phenyl-1,3-thiazolidine-4-carboxylic acid 

Relevant articles and documents

New aspects of the formation of 2-substituted thiazolidine-4-carboxylic acids and their thiohydantoin derivatives

Aromatic aldehydes reacted readily with (R)-cysteine in boiling acidified methanol to give diastereomeric mixtures of the corresponding 2-(aryl substituted) thiazolidine-4-carboxylic acids. 4-Nitrobenzaldehyde under similar conditions afforded one isomer of 2-(4-nitrophenyl)-thiazolidine-4-carboxylic acid, which epimerized in the NMR solvents into a diastereomeric mixture. 2-Nitrobenzaldehyde reacted with (R)-cysteine to afford 3,5-bis-(2-nitrophenyl)-tetrahydro-1H-thiazolo[3,4-c]oxazol-1-one as the sole product, which collapsed in the NMR solvent into a diastereomeric mixture of the thiazolidine-4-carboxylic acids. The thiazolidine derivatives reacted smoothly with phenyl isothiocyanate to give single isomers of the corresponding thiohydantoins.

2-Substituted 4,5-dihydrothiazole-4-carboxylic acids are novel inhibitors of metallo-β-lactamases

Bacterial resistance to β-lactam antibiotics caused by class B metallo-β-lactamases (MBL), especially for certain hospital-acquired, Gram-negative pathogens, poses a significant threat to public health. We report several 2-substituted 4,5-dihydrothiazole-4-carboxylic acids to be novel MBL inhibitors. Structure activity relationship (SAR) and molecular modeling studies were performed and implications for further inhibitor design are discussed.

Novel substituted 2-(6-benzyl-5-oxo-3-phenyl-(S3,7S,7AR)- pherhydroimidazol (1,5-C) (1,3) thiazol-7YL) compounds

A novel route has been developed for substituted 2-[-6-benzyl-5-oxo-3-phenyl-(3s,7s,7aR)-perhydroimidazol[1,5-c][1,3]thiazol] compounds; crucial intermediates for D(+)-biotin of formula (7) which involves simple, efficient, practical and cost effective protocol. These are crucial intermediates for commercially important D(+)-biotin preparation. These compounds are more stable and are produced by non-hazardous methods.