Al-Soud Yaseen A, Al-Masoudi Najim A, Schuppler Thilo, De Clercq Erik, Pannecouque Christophe
Department of Chemistry, College of Science, University of Al al-Bayt, Al-Mafraq, Jordan.
Nucleosides Nucleotides Nucleic Acids. 2008 May;27(5):469-83. doi: 10.1080/15257770802088829.
Microwave-assisted synthesis of novel acyclic C-nucleosides of 6-alkyl/aryl-3-(1,2-O-isopropylidene-D-ribo-tetritol-1-yl)[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles (5-12) and the 6-aryl-thiomethyl analogues 25-27 has been described. Deblocking of 5-12 and 25-27 afforded the free acyclic C-nucleosides 13-20, and 28-30, respectively. All of the synthesized compounds showed no inhibition against HIV-1 and HIV-2 replication in MT-4 cells. However, 6-(3,4-dichlorophenyl)-3-(1,2-O-isopropylidene-D-ribo-tetritol-1-yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole (6) is a potent inhibitor, in vitro, of the replication of HIV-2. These results suggest that compound 6 should be considered as a new lead in the development of antiviral agent.
已报道了微波辅助合成新型无环C-核苷，即6-烷基/芳基-3-(1,2-O-异亚丙基-D-核糖四醇-1-基)[1,2,4]三唑并[3,4-b][1,3,4]噻二唑(5-12)以及6-芳基硫甲基类似物25-27。对5-12和25-27进行脱保护分别得到游离的无环C-核苷13-20和28-30。所有合成化合物在MT-4细胞中均未显示出对HIV-1和HIV-2复制的抑制作用。然而，6-(3,4-二氯苯基)-3-(1,2-O-异亚丙基-D-核糖四醇-1-基)-7H-1,2,4-三唑并[3,4-b][1,3,4]噻二唑(6)在体外是HIV-2复制的有效抑制剂。这些结果表明化合物6应被视为抗病毒药物开发中的新先导物。
