title: Synthesis and anti-HIV-1 activity of 4-substituted-7-(2'-deoxy-2'-fluoro-4'-azido-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine analogues.
abstract: Three novel 4-subsituted-7-(2'-deoxy-2'-fluoro-4'-azido-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine analogues were designed, synthesized, and tested for their anti-HIV-1 activity. Initial biological studies indicated that among these pyrrolo[2,3-d]pyrimidine ribonucleoside analogues, 4-amino-7-(2'-deoxy-2'-fluoro-4'-azido-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine 10 exhibited the most potent anti-HIV-1 activity (EC(50)=0.5±0.3 μM), while 4-hydroxy-7-(2'-deoxy-2'-fluoro-4'-azido-β-D-ribofuranosyl)pyrrolo[2,3-d] pyrimidine 9 and 4-amino-5-fluoro-7-(2'-deoxy-2'-fluoro-4'-azido-β-D-ribofuranosyl)pyrrolo[2,3-d] pyrimidine 11 showed moderate activity (EC(50)=13±8 and 5.4±0.3 μM, respectively). The cytotoxicity of these compounds has also been assessed. No significant cytotoxicities were found for any of these compounds with concentrations up to 25 μM.
authors.affiliation: The Fine Chemical Key Lab. of Henan Province, Henan Academy of Sciences, Zhengzhou 450002, PR China.
authors.forename: Xiaohe
authors.initials: X
authors.lastname: Guo
authors.forename: Yujiang
authors.initials: Y
authors.lastname: Li
authors.forename: Le
authors.initials: L
authors.lastname: Tao
authors.forename: Qiang
authors.initials: Q
authors.lastname: Wang
authors.forename: Shuyang
authors.initials: S
authors.lastname: Wang
authors.forename: Weidong
authors.initials: W
authors.lastname: Hu
authors.forename: Zhenliang
authors.initials: Z
authors.lastname: Pan
authors.forename: Qinghua
authors.initials: Q
authors.lastname: Yang
authors.forename: Yanmei
authors.initials: Y
authors.lastname: Cui
authors.forename: Zhaopeng
authors.initials: Z
authors.lastname: Ge
authors.forename: Lihong
authors.initials: L
authors.lastname: Dong
authors.forename: Xuejun
authors.initials: X
authors.lastname: Yu
authors.forename: Haoyun
authors.initials: H
authors.lastname: An
authors.forename: Chuanjun
authors.initials: C
authors.lastname: Song
authors.forename: Junbiao
authors.initials: J
authors.lastname: Chang
mesh_terms: D019380:Anti-HIV Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D015658:HIV Infections / Q000188:drug therapy; D015497:HIV-1 / Q000187:drug effects*; D006801:Humans; D011743:Pyrimidines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D012263:Ribonucleosides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D019380:Anti-HIV Agents; D011743:Pyrimidines; D011758:Pyrroles; D012263:Ribonucleosides