Synthesis and Characterization of New 3^″,5^″-DIARYL-3^″H-Dispiropyran/Thiopyran[4,2′-Chroman-3′,2^″-[1,3,4-Thiadiazol]-4′-One Derivatives and Related Compounds as Anticancer and Antiviral Agents

GRAPHICAL ABSTRACT

Abstract

A series of 3^″,5^″-diaryl-3^″H-dispiropyran/thiopyran[4,2′-chroman-3′,2^″-[1,3,4-thiadiazol]-4′-ones 5a-n were synthesized from the reaction of trispiro[tetrahydropyran(tetrahydrothiopyran)-4,5′-2H-chromeno-[3,4-e][1,3,4]oxadithiin-2′,3^″-chroman-2^″4′^″-tetrahydropyran-(tetrahydrothiopyran)]-4^″-ones 3a,b with nitrilimines (generated in situ via triethylamine dehydrohalogenation of the corresponding hydrazonoyl chlorides). A single crystal diffraction of compound 5a adds support for the established structure. The results of the anticancer evaluation against human breast adenocarcinoma MCF-7 cell line through inhibiting of human tyrosine kinase showed that most of the tested compounds possess antiproliferative activity as potent to moderate growth inhibitory activity, especially compounds 3b, 5a, 5c, 5e, 5g, and 5k. Also, the prepared compounds were tested against rotavirus Wa strain and adenovirus type 7 and the results showed that two compounds (5e,n) were active.

Keywords:

• Pyran-4-one
• thiopyran-4-one
• chroman-4-one
• 1,3,4-thiadiazol
• anticancer
• antiviral agents

ACKNOWLEDGMENT

The authors extend their thanks to the National Research Centre (Dokki, Giza, Egypt) for all the given facilities.