engleski

Synthesis and biological activity of novel 1,2,3- triazole derivatives of benzoxazole

Cancer is a complex, prevalent and fatal disease that notably affects almost every tissue in the human body, and many anticancer drugs are currently being used clinically for the treatment of several malignancies. [1] However, solid tumors such as breast cancer, resist most of the clinically-available anticancer agents probably due to gene mutations or epigenetic modifications during the course of therapy that affect the uptake, metabolism of efflux of drugs from cancer cells. Benzoxazoles derivatives show significant pharmacophoric behavior with diverse range of biological activities including antitumor activity. [2, 3] In this paper, we present the synthesis of novel 1, 2, 3-triazolyl benzoxazole derivatives by using click reaction in deep eutectic solvents (DES). The key precursors of Schiff bases were synthesized by ultrasound irradiation, and subsequent cyclization reaction with NaCN gave the corresponding 2-arlybenzoxazoles which are furthermore converted to O-propargylated benzoxazole derivatives by microwave assisted alkylation reactions. 1, 2, 3-triazolyl benzoxazole derivatives were prepared by click-reaction of O-propargylated benzoxazole derivatives with corresponding azides in DES (ChCl/glycerol). All synthesized compounds were evaluated against Gram-positive and Gram-negative bacterial strains as well as malignant tumor cell lines. 2-(4-(2-morpholinoethoxy)phenyl)benzoxazole showed the most pronounced activity against non-small-cell lung cancer cell lines (NCI-H460, IC50=0.4 µM).

benzoxazoles, antitumor activity, antimicrobial activity

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