Toward Developing Therapies against Corona Virus: Synthesis and Anti-Avian Influenza Virus Activity of Novel Cytosine Thioglycoside Analogues

Mamdouh A Abu-Zaied; Nashwa M Mahmoud; Galal H Elgemeie

doi:10.1021/acsomega.0c01537

Toward Developing Therapies against Corona Virus: Synthesis and Anti-Avian Influenza Virus Activity of Novel Cytosine Thioglycoside Analogues

ACS Omega. 2020 Aug 6;5(32):20042-20050. doi: 10.1021/acsomega.0c01537. eCollection 2020 Aug 18.

Authors

Mamdouh A Abu-Zaied¹, Nashwa M Mahmoud², Galal H Elgemeie³

Affiliations

¹ Green Chemistry Department, National Research Centre, 33 El Bohouth Street, Dokki, Giza 12622, Egypt.
² Chemistry Department, Faculty of Science, Suez University, Suez 43511, Egypt.
³ Chemistry Department, Faculty of Science, Helwan University, Helwan, Cairo 11731, Egypt.

Abstract

A series of pyrimidine and pyrimidine thioglycoside derivatives were newly synthesized using sodium 2-cyano-3-(arylamino)prop-1-ene-1,1-bis(thiolates) and urea to give the corresponding sodium 6-amino-5-aryl-2-oxo-1,2-dihydropyrimidine-4-thiolates. Stirring of the latter with peracetylated α-d-gluco- and galacto-pyranosyl bromides in DMF afforded the corresponding pyrimidine thioglycosides. On the other hand, treatment of 6-amino-5-aryl-2-oxo-1,2-dihydropyrimidine-4-thiolate salts with hydrochloric acid produced the corresponding pyrimidine-4-thioles, which on stirring with α-d-gluco- and galacto-pyranosyl bromides in sodium hydride and DMF gave the corresponding pyrimidine thioglycosides. Deacetylation of the protected pyrimidine thioglycosides gave the corresponding free pyrimidine thioglycosides. The synthesized compounds have been characterized by ¹³C NMR, ¹H NMR, and IR spectroscopy. The pyrimidine thioglycosides and free pyrimidine thioglycosides were tested against avian influenza H5N1 virus strain and exhibited highest to moderate activity.