New Potent SARS-CoV 3C-Like Protease Inhibitors Derived from Thieno[2,3-d]-pyrimidine Derivatives

Archiv der Pharmazie
Amira S Abd El-AllMohamed M Abdalla

Abstract

2-Amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (1) condensed with carbaldehydes 2a,b to give the respective thienopyrimidines (3a,b), which reacted with phosphoryl chloride and hydrazine hydrate to afford the respective pyrimidinohydrazines (4a,b). Compound 4a condensed with acetophenone under Vilsmeier conditions to afford the formylated pyrazolopyrimidine 6. Condensation of 4a with active methylenes produced the respective pyrazolopyrimidines (7-11). Besides, 4a condensed with succinic anhydride and with phthalic anhydride, yielding the pyrrolidine-2,5-dione 12 and the isoindoline-1,3-dione 13, respectively. Moreover, 4a reacted with isatin to afford the hydrazono-indolin-2-one 14. Structural elucidations for the new thienopyrimidines were based upon compatible analytical and spectroscopic results. Eleven of the new compounds were tested and found active against influenza A neuraminidase virus (H3N2). Compounds 12 and 13 were the most potent.

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Citations

Dec 31, 2020·Bioorganic Chemistry·Zefeng ZhaoXiaohui Zheng
Jul 27, 2021·Russian Chemical Bulletin = Izvestii︠a︡ Akademii Nauk. Serii︠a︡ Khimicheskai︠a︡·S S ShatokhinÉ T Oganesyan

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