Issue 8, 2015

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

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

Supplementary files

Article information

Article type
Concise Article
Submitted
02 Apr 2015
Accepted
08 Jun 2015
First published
10 Jun 2015

Med. Chem. Commun., 2015,6, 1464-1470

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

A. Zablotskaya, I. Segal, A. Geronikaki, G. Kazachonokh, Y. Popelis, I. Shestakova, V. Nikolajeva and D. Eze, Med. Chem. Commun., 2015, 6, 1464 DOI: 10.1039/C5MD00140D

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements