Thiosugar nucleosides. Synthesis and biological activity of 1,3,4-thiadiazole, thiazoline and thiourea derivatives of 5-thio-D-glucose.
New acylated 5-thio-beta-D-glucopyranosylimino-disusbstituted 1,3,4-thiadiazols 8, and 11 were prepared, via spontaneous rearrangements, by cycloaddition of the glycosyl isothiocyanate 2 with the reactive intermediates 1-aza-2-azoniaallene hexachloroantimonates 4 and 6, respectively. Reaction of 2 with aminoacetone or chloroethylamine afforded the acylated 5-thio-beta-D-glucopyranosyl-4-imidazoline-2-thione nucleoside 16 and glucopyranosylamino-2-thiazoline derivative 18, respectively. Deblocking of 8, 11, 17 and 19 furnished the free nucleoside analogues 9, 12, 18 and 20, respectively. Analogously, treatment of 2 with chloroethylamine in the 1:2 ratio afforded the thioureylendisaccharide 21. No in vitro antiviral activity against HIV-1, HIV-2, human cytomegallovirus (HMCV), has been found for the new synthesized compounds.
Al-Masoudi
Najim A
NA
Department of Chemistry, University of Konstanz, Konstanz, Germany. Najim.Al-Masoudi@gmx.de
Al-Soud
Yaseen A
YA
Al-Masoudi
Wasfi A
WA
D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002460:Cell Line; D005947:Glucose / Q000031:analogs & derivatives* / Q000737:chemistry*; D006801:Humans; D013830:Thiadiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013844:Thiazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D013863:Thioglucosides / Q000138:chemical synthesis / Q000378:metabolism; D013872:Thionucleosides / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology*; D013890:Thiourea / Q000737:chemistry* / Q000494:pharmacology
D019380:Anti-HIV Agents; D013830:Thiadiazoles; D013844:Thiazoles; D013863:Thioglucosides; D013872:Thionucleosides; C058949:1,3,4-thiadiazole; C003002:5-thio-D-glucose; D013890:Thiourea; D005947:Glucose