Synthesis of substituted thieno[2,3-d]pyrimidine-2,4-dithiones and their S-glycoside analogues as potential antiviral and antibacterial agents.
Previously, we synthesized and evaluated several thienopyrimidine derivatives containing heterocyclic ring substituents linked to the pyrimidine-2-thione nucleus at C-2 by a two- to four-atom spacer as potential anti-HIV-1 and antimicrobial agents. Also, from the literature, S-substituted pyrimidin-4-ones A and B exhibited interesting anti-HIV-1 activity. To further investigate the synthesis, tools and biological activities, we synthesized several new thienopyrimidine derivatives derived from thieno[2,3-d]-pyrimidine-2,4-dithione (3a,b) The compounds were designed to comprise the heterocyclic substituents directly linked to the thienopyrimidines nucleus at C-2. Moreover, various related triazolo[4,3-a]benzothieno[2,3-d]pyrimidines derived from 2-thioxothienopyrimidine were also prepared as isosteres. Among the synthesized derivatives 3-18, the compounds 3a, 8a, 10a, 13a and 14a were showing complete inhibition at 128 mg/mL or less.
Hafez
Hend N
HN
Photochemistry Department (Heterocyclic& Nucleosides Group), National Research Centre, 12622 Dokki, Cairo, Egypt.
Hussein
Hoda A R
HA
El-Gazzar
Abdel-Rahman B A
AR
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D006027:Glycosides / Q000737:chemistry*; D015497:HIV-1 / Q000187:drug effects; D018259:Herpesvirus 1, Human / Q000187:drug effects; D020128:Inhibitory Concentration 50; D011743:Pyrimidines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
D000900:Anti-Bacterial Agents; D000998:Antiviral Agents; D006027:Glycosides; D011743:Pyrimidines