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Synthesis, Structure and Structure-Activity Relationship Analysis of 3-tert-butoxycarbonyl-2-arylthiazolidine-4-carboxylic Acid Derivatives as Potential Antibacterial Agents

Synthesis, Structure and Structure-Activity Relationship Analysis of 3-tert-butoxycarbonyl-2-arylthiazolidine-4-carboxylic Acid Derivatives as Potential Antibacterial Agents

Zhong-Cheng Song, Gao-Yuan Ma, Peng-Cheng Lv, Huan-Qiu Li, Zhu-Ping Xiao, Hai-Liang Zhu

Eur J Med Chem. 2009 Oct;44(10):3903-8.

PMID: 19423200

Abstract:

Nine 2-arylthiazolidine-4-carboxylic acid derivatives and nine 3-tert-butoxycarbonyl-2-arylthiazolidine-4-carboxylic acid derivatives were synthesized to screen for their antibacterial activities. Compounds 5, 14-18 were first reported. Their chemical structures were clearly determined by (1)H NMR, (13)C NMR, ESI mass spectra and elemental analyses, coupled with one selected single-crystal structure. All the compounds were assayed for antibacterial activities against two Gram-positive bacterial strains (Bacillus subtilis ATCC 6633 and Staphylococcus aureus ATCC 6538) and two Gram-negative bacterial strains (Escherichia coli ATCC 35218 and Pseudomonas aeruginosa ATCC 13525) by MTT method. Most of the 3-tert-butoxycarbonyl-2-arylthiazolidine-4-carboxylic acid derivatives exhibited better antibacterial activities against the four bacterial strains than relative 2-arylthiazolidine-4-carboxylic acid derivatives. Compound (2RS,4R)-3-(tert-butoxycarbonyl)-2-(5-fluoro-2-hydroxyphenyl)thiazolidine-4-carboxylic acid (14) showed powerful antibacterial activities against P. aeruginosa with IC(50) value of 0.195 microg/mL, which was superior to the positive controls Penicillin G and Kanamycin B, respectively. On the basis of the biological results, structure-activity relationships were discussed.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
LS7931189	1-(tert-Butoxycarbonyl)-6-chloro-1H-indol-2-ylboronic acid			Price

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