methyl 2α-{1N[1-(2-deoxy-2β-fluoro-β-D-arabinopentafuranosyl)uracil-4-yl]-1H-1,2,3 triazole-4-yl}-3β-hydroxylup-20(29)-en-28-oate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl 2α-{1N[1-(2-deoxy-2β-fluoro-β-D-arabinopentafuranosyl)uracil-4-yl]-1H-1,2,3 triazole-4-yl}-3β-hydroxylup-20(29)-en-28-oate
• 英文别名: methyl (1R,3aS,5aR,5bR,7aR,9S,10S,11aR,11bR,13aR,13bR)-10-[[1-[(2R,3R,4S,5R)-5-(2,4-dioxopyrimidin-1-yl)-4-fluoro-3-hydroxy-2-(hydroxymethyl)oxolan-2-yl]triazol-4-yl]methyl]-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylate
• 化学式: C₄₃H₆₂FN₅O₈
• 分子量: 795.992
• InChiKey: FDWQETRCAZCSOW-WALJNYEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  57
• 可旋转键数：
  8
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  176
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  路路通酸 在 sodium tetrahydroborate 、 双(三甲基硅烷基)氨基钾 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 水 、 异丙醇 、 叔丁醇 为溶剂， 反应 36.75h， 生成 methyl 2α-{1N[1-(2-deoxy-2β-fluoro-β-D-arabinopentafuranosyl)uracil-4-yl]-1H-1,2,3 triazole-4-yl}-3β-hydroxylup-20(29)-en-28-oate
  参考文献：
  名称：

  Novel Betulinic Acid–Nucleoside Hybrids with Potent Anti-HIV Activity

  摘要：

  Novel betulinic/betulonic acid-nucleoside hybrids were synthesized as possible new anti-HIV agents. Among the synthesized hybrids, two compounds were highly effective against HIV. Compared with AZT and DSB, compounds 10a (IC50 = 0.0078 mu M, CC50 = 9.6 mu M) and 10b (IC50 = 0.020 mu M, CC50 = 23.8 mu M) showed more potent or equipotent, respectively, antiHIV activity but displayed lower cytotoxicity.

  DOI：

  10.1021/acsmedchemlett.0c00414

文献信息

• Novel Betulinic Acid–Nucleoside Hybrids with Potent Anti-HIV Activity
  作者：Qiang Wang、Yujiang Li、Liyun Zheng、Xiaowan Huang、Yanli Wang、Chin-Ho Chen、Yung-Yi Cheng、Susan L. Morris-Natschke、Kuo-Hsiung Lee

  DOI：10.1021/acsmedchemlett.0c00414

  日期：2020.11.12

  Novel betulinic/betulonic acid-nucleoside hybrids were synthesized as possible new anti-HIV agents. Among the synthesized hybrids, two compounds were highly effective against HIV. Compared with AZT and DSB, compounds 10a (IC50 = 0.0078 mu M, CC50 = 9.6 mu M) and 10b (IC50 = 0.020 mu M, CC50 = 23.8 mu M) showed more potent or equipotent, respectively, antiHIV activity but displayed lower cytotoxicity.