Synthesis and Biological Evaluation of Thiazolyl-Ethylidene Hydrazino-Thiazole Derivatives: A Novel Heterocyclic System

Abstract

The reaction of 2-(1-(2-(2-(4-methoxybenzylidene)hydrazinyl)-4-methylthiazol-5-yl)ethylidene)hydrazinecarbothioamide with a range of hydrazonoyl chlorides and α-halo-compounds yielded three new series of thiazole derivatives. Chemical and physical techniques were used to analyze all newly prepared derivatives (1H-NMR, 13C-NMR, FT-IR and mass spectrometry). The potential antimicrobial and anticancer properties of the synthesized derivatives were investigated using various in vitro biological experiments. Most of the thiazole compounds tested were effective against Gram-positive and Gram-negative bacteria. In addition, a minimum inhibition concentration was determined for the antibiotic properties of the most active produced substances. The cytotoxic activities were tested on HepG-2 (liver carcinoma), HCT-116 (colorectal carcinoma) and MDA-MB-231 (breast carcinoma) cell lines in comparison with cisplatin reference drug and using colorimetric MTT assay. The results detected that compound 10c was the most potent against the three tested cell lines. Interestingly, when the tested compounds were evaluated for their toxicity against normal (MRC-5) cells, they exhibited low toxic effects indicating the safe use of most of them that may require further in vivo and pharmacological studies.

Keywords

• hydrazones
• thiazoles
• hydrazonoyl halides
• cyclization
• cytotoxicity
• antimicrobial activity