Synthesis and antibacterial activity of new (2,4-dioxothiazolidin-5-yl/ylidene)acetic acid derivatives with thiazolidine-2,4-dione, rhodanine and 2-thiohydantoin moieties

Saudi Pharmaceutical Journal : SPJ : the Official Publication of the Saudi Pharmaceutical Society
Nazar TrotskoAnna Malm

Abstract

A series of new (2,4-dioxothiazolidin-5-yl/ylidene)acetic acid derivatives with thiazolidine-2,4-dione, rhodanine and 2-thiohydantoin moiety (28-65) were synthesized by the reaction of (2,4-dioxothiazolidin-5-yl/ylidene)acetic acid chlorides with 5-(hydroxybenzylidene) thiazolidine-2,4-dione, rhodanine and 2-thiohydantoin derivatives. Obtained compounds (28-65) were tested on reference strains of Gram-positive bacteria and ones of the Gram-negative bacteria. The antibacterial activity of target compounds was determined by broth microdilution method. These derivatives showed antibacterial activity generally against Gram-positive bacterial strains. Most active compounds possess MIC = 3.91 mg/L. Our results suggest that presence of electron-withdrawing substituent at phenyl ring is favorable while geometry of molecule does not play important role in antibacterial response. It was confirmed the lack of direct influence of substitution pattern at phenyl ring on antibacterial activity of closely related compounds of series 1-3. The antibacterial activity of some compounds was similar or higher than the activity of commonly used reference drugs such as oxacillin and cefuroxime.

Citations

Apr 4, 2019·Artificial Cells, Nanomedicine, and Biotechnology·Seyyed Mojtaba MousaviAli Mohammad Amani
Nov 30, 2019·Expert Opinion on Drug Discovery·Suresh MaddilaSreekantha B Jonnalagadda
Aug 24, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Nazar TrotskoKatarzyna Dzitko
Mar 25, 2020·Topics in Current Chemistry·Nusrat SahibaShikha Agarwal
Apr 28, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Nazar TrotskoMonika Wujec
Mar 20, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Nazar TrotskoMonika Wujec
Feb 16, 2021·European Journal of Medicinal Chemistry·Nazar Trotsko

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