Synthesis and Molecular Docking of Some Novel Thiazoles and Thiadiazoles Incorporating Pyranochromene Moiety as Potent Anticancer Agents

Abstract

Background: Chemotherapy has become one of the methods that are being adopted to treat cancer. Coumarins, thiazoles and thiadiazoles are versatile synthetic scaffolds possessing wide spectrum of biological effects including potential anticancer activity.

Objective: In the efforts to develop suitable anticancer drugs, medicinal chemists have focused on coumarin derivatives. A series of novel thiazole-pyranochromene and thiadiazole-pyranochromene derivatives were synthesized via heterocyclization of varies hydrazonoyl halides with methyl pyrano[3,2- g]chromen-3-yl)ethylidene)hydrazine-1-carbodithioate and pyrano[3,2-g]chromen-3-yl)ethylidene)- hydrazine-1-carbothioamide, respectively.

Method: All the newly synthesized compounds have been characterized on the basis of elemental analysis and spectral data (IR, 1H and 13C NMR, Mass). Moreover, all the products were evaluated for their anticancer activity against HEPG2-1.

Results: The results revealed that six new compounds showed promising anticancer activity.

Conclusion: In the present paper, 3-acetyl-5-methoxy-8-methyl-2H,6H-pyrano[3,2-g]chromene-2,6- dione proved to be a useful precursor for synthesis of various 1,3-thiazoles and 1,2,4-thiadiazoles incorporating pyrano[3,2-g]chromene moiety as anticancer agents. The computational studies using MOE 2014.09 software are confirming the results in biological activity.

Keywords: Pyranochromene; antitumor activity; hydrazonoyl halides; molecular docking studies; thiadiazoles; thiazoles..