Synthesis, Reactions, and Antiviral Activity of 6′-Amino-2′-thioxo-1′,2′-dihydro-3,4′-bipyridine-3′,5′-dicarbonitrile

Abstract

Nicotinaldehyde 1 reacted with 2-cyanoethanethioamide 2to give 2-cyano-3-pyridin-3-ylprop-2-enethioamide 3, which reacted with a second mole of 2to give the corresponding 6′-amino-2′-thioxo-1′,2′-dihydro-3,4′-bipyridine-3′,5′-dicarbonitrile 6. The synthetic potentiality of compound 6 was investigated via its reaction with active halogen-containing reagents, e.g., chloroacetone, 2-chloro-3-oxobutanoate, 2-chloroacetamide, chloroaceto-nitrile, and ethyl chloroacetate, to afford the corresponding thieno[2,3-b]-pyridine derivatives. Structure elucidation of all newly synthesized heterocyclic compounds was based on the data of elemental analyses, and IR, ¹ H NMR, as well as mass spectra. Cytotoxicity, anti–HSV1, anti–HAV, and MBB activities were evaluated for all newly synthesized heterocyclic compounds.

Keywords:

• 2-Cyano-3-pyridin-3-yl-prop-2-enethioamide
• 2-cyanoethanethioamide
• bipyridine-3′
• 5′-dicarbonitrile
• nicotinaldehyde
• thieno[2,3-b]pyridine