RESUMO
Silylated 4-methylthiouracil and 4-methylthiothymine were condensed in the presence of TMS triflate with methyl 2,3-dideoxy-3-fluoro-5-O-(4- phenylbenzoyl)-D-erythro-pentofuranoside (3) and methyl 3-azido-5-O- (tert-butyldiphenylsilyl)-2,3-dideoxy-D-erythro-pentofuroside++ + (8), respectively, to give the corresponding nucleosides which were deprotected. The 3'-azido nucleoside was reduced with triphenylphosphine to the corresponding 3'-amino nucleoside. The 3'-amino nucleoside was also obtained by condensation of 4-methylthiothymidine with a 3-phthalimido sugar 14 followed by deprotection. The 4-methylthio analogue 11 of AZT showed moderate activity against HIV.
Assuntos
Antivirais/síntese química , Didesoxinucleosídeos/síntese química , HIV-1/efeitos dos fármacos , Zidovudina/análogos & derivados , Zidovudina/síntese química , Antivirais/farmacologia , Didesoxinucleosídeos/farmacologia , Zidovudina/farmacologiaRESUMO
Thiaxanthen-9-ol (1) was condensed with nitriles 2a-e to yield the thiaxanthen-9-yl-acetonitriles 3a-e. With the thiols 7a-d, 1 yielded the thioethers 8a-d.