4-hydroxy-7-(2'-deoxy-2'-fluoro-4'-azido-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine | 1345193-59-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: 4-hydroxy-7-(2'-deoxy-2'-fluoro-4'-azido-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine
• 英文别名: 7-[(2R,3S,4R,5R)-5-azido-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrrolo[2,3-d]pyrimidin-4-ol；7-[(2R,3S,4R,5R)-5-azido-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-pyrrolo[2,3-d]pyrimidin-4-one
• CAS: 1345193-59-0
• 化学式: C₁₁H₁₁FN₆O₄
• 分子量: 310.245
• InChiKey: OGBVLDBUIBYRKU-JRPBRRGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-氯-7-(3,5-二-O-苯甲酰基-2-脱氧-2-氟-beta-D-阿拉伯呋喃糖基)-7H-吡咯并[2,3-d]嘧啶 在 咪唑 、 4-二甲氨基吡啶 、 dipotassium hydrogenphosphate 、 三甲基氯硅烷 、 sodium azide 、 氨 、 碘 、 四丁基硫酸氢铵 、 一氯化碘 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 间氯过氧苯甲酸 、 三苯基膦 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 50.08h， 生成 4-hydroxy-7-(2'-deoxy-2'-fluoro-4'-azido-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine
  参考文献：
  名称：

  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

  摘要：

  Three novel 4-subsituted-7-(2'-deoxy-2'-fluoro-4'-azido-beta-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-beta-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine 10 exhibited the most potent anti-HIV-1 activity (EC50 = 0.5 +/- 0.3 mu M), while 4-hydroxy-7-(2'-deoxy-2'-fluoro-4'-azido-beta-D-ribofuranosyl)pyrrolo[ 2,3-d]pyrimidine 9 and 4-amino-5-fluoro-7-(2'-deoxy-2'-fluoro-4'-azido-beta-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine 11 showed moderate activity (EC50 = 13 +/- 8 and 5.4 +/- 0.3 mu M, 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 mu M. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.040

文献信息

• 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
  作者：Xiaohe Guo、Yujiang Li、Le Tao、Qiang Wang、Shuyang Wang、Weidong Hu、Zhenliang Pan、Qinghua Yang、Yanmei Cui、Zhaopeng Ge、Lihong Dong、Xuejun Yu、Haoyun An、Chuanjun Song、Junbiao Chang

  DOI：10.1016/j.bmcl.2011.09.040

  日期：2011.11

  Three novel 4-subsituted-7-(2'-deoxy-2'-fluoro-4'-azido-beta-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-beta-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine 10 exhibited the most potent anti-HIV-1 activity (EC50 = 0.5 +/- 0.3 mu M), while 4-hydroxy-7-(2'-deoxy-2'-fluoro-4'-azido-beta-D-ribofuranosyl)pyrrolo[ 2,3-d]pyrimidine 9 and 4-amino-5-fluoro-7-(2'-deoxy-2'-fluoro-4'-azido-beta-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine 11 showed moderate activity (EC50 = 13 +/- 8 and 5.4 +/- 0.3 mu M, 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 mu M. (C) 2011 Elsevier Ltd. All rights reserved.