Synthesis and biological evaluation of lipid-like 5-(2-hydroxyethyl)-4-methyl-1,3-thiazole derivatives as potential anticancer and antimicrobial agents?

MedChemComm Pub Date: 2015-06-10 DOI: 10.1039/C5MD00140D

Abstract

A series of new lipid-like thiazole derivatives have been synthesized in good yields by O-alkylation of 5-(2-hydroxyethyl)-4-methyl-1,3-thiazole, a thiamine metabolite, under phase transfer catalysis conditions followed by N-alkylation with the aim to obtain potential anticancer and antimicrobial agents. The synthesized cationic amphiphiles and their ether precursors were subjected to in vitro cytotoxic evaluation against monolayer human fibrosarcoma HT-1080 and mouse hepatoma MG-22A tumour cell lines and normal mouse NIH 3T3 fibroblasts and were screened for antimicrobial activity concerning gram-positive and gram-negative bacterial and fungal strains. The synthesized compounds possessed strong antimicrobial activity, significant selective cytotoxicity and high NO-induction ability. In vivo investigation of 3,4-dimethyl-5-(2-undecyloxyethyl)-1,3-thiazol-3-ium iodide confirmed anticancer action, reliably inhibiting mouse sarcoma S-180 tumour growth.

Graphical abstract: Synthesis and biological evaluation of lipid-like 5-(2-hydroxyethyl)-4-methyl-1,3-thiazole derivatives as potential anticancer and antimicrobial agents
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