Synthesis of 1,6-bis(semicarbazide)hexanes and 1,6-bis(1,2,4-triazol-5-one)hexanes and their antiproliferative and antimicrobial activity

Abstract

A series of 1,6-bis(3-substituted-4,5-dihydro-1H-1,2,4-triazol-5-on-4- yl)hexanes (3a-g) were synthesized by the cyclization reaction of 1,6-bis(1- substituted-semicarbazide-4-yl)hexanes (2a-g) in alkaline medium. New derivatives (3a-c) were screened in vitro for their antiproliferative and anticancer activity in human tumor cell lines derived from breast and lung carcinoma cells. Compounds 3a (in concentration of 0.18 mM), 3b (in concentrations of 0.12 mM and 0.02 mM) and 3c (in concentrations of 0.23 mM and 0.11 mM) were found to be the most effective against lung cell line. The compound (3a) had the most antiproliferative effect on breast carcinoma cell line. Representative compounds were established and evaluated as antimicrobial agents. All tested derivatives showed MIC in range 1.87-7.5 (μg/mL). The compound (3b) was the most effective against C. albicans (MIC 1.87 μg/mL).

Keywords

• synthesis
• semicarbazide
• 1,2,4-triazole
• biological activity