5-Ethoxymethylidene-4-thioxo-2-thiazolidinone as Versatile Building Block for Novel Biorelevant Small Molecules with Thiopyrano[2,3-d][1,3]thiazole Core

Abstract

5-Ethoxymethylidene-4-thioxo-2-thiazolidinone was studied as versatile core building block in the synthesis of new thiopyrano[2,3-d]thiazole derivatives relevant for medicinal chemistry purposes under hetero-Diels–Alder reaction conditions. Promising compounds (6, 10) were identified among synthesized series with high antitumor and moderate antiviral activity.

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GRAPHICAL ABSTRACT

Keywords:

• Biological activity
• 5-ethoxymethylidene-4-thioxo-2-thiazolidinone
• hetero-Diels–Alder reaction
• thiopyrano[2,3-d]thiazole

ACKNOWLEDGMENTS

We are grateful to V. L. Narayanan from Drug Synthesis and Chemistry Branch, National Cancer Institute, Bethesda, MD, USA, for in vitro evaluation of anticancer activity and to Chris Tseng, from Division of Microbiology and Infectious Diseases, NIAID/NIH, Bethesda, MD, USA, for in vitro evaluation of antiviral activity.