Synthesis and antitumor activity of fluoroquinolon-3-yl s-triazole sulfanylacetylhydrazones and s-triazole hydrazone derivatives (V) / 中国药学杂志

ABSTRACT

OBJECTIVE: To explore an efficient modification strategy for conversion of antibacterial fluoroquinolones to antitumor ones. METHODS: An azole heterocyclic ring, s-triazole, as a bioisotere of the C-3 carboxylic acid for ofloxacin(1), functional acyl-hydrazones and hydrazones, was used as the modified side-chain for the C-3 bioisotere, then the C-3 s-triazole acylhydrazones and s-triazole hydrazone derivatives were designed and their in vitro antitumor activity was evaluated by MTT assay. RESULTS: Fourteen target compounds were synthesized, and they exhibited stronger antitumor activity than the parent ofloxacin. And most importantly, hydrazone derivatives had higher activity than their corresponding acylhydrazone compounds. CONCLUSION: s-Triazole-hydrazone moiety is warranted special attention as an efficient bioisosteric replacement of the C-3 carboxylic acid for further development of antitumor fluoroquinolone lead compounds.