(1R,2R,5S,8S,9R,10R,13R,14R,20R)-N-(7-acetamidoheptyl)-1,2,14,19,19-pentamethyl-17-oxo-8-propan-2-yl-18-oxapentacyclo[11.9.0.02,10.05,9.014,20]docosane-5-carboxamide | 1550232-85-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (1R,2R,5S,8S,9R,10R,13R,14R,20R)-N-(7-acetamidoheptyl)-1,2,14,19,19-pentamethyl-17-oxo-8-propan-2-yl-18-oxapentacyclo[11.9.0.02,10.05,9.014,20]docosane-5-carboxamide
• CAS: 1550232-85-3
• 化学式: C₃₉H₆₆N₂O₄
• 分子量: 626.964
• InChiKey: IORIGQMNQXGAES-WHKYHWPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  45
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  84.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2R,5S,8S,9R,10R,13R,14R,20R)-N-(7-acetamidoheptyl)-1,2,14,19,19-pentamethyl-17-oxo-8-propan-2-yl-18-oxapentacyclo[11.9.0.02,10.05,9.014,20]docosane-5-carboxamide 在 硫酸 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 3-[(3S,4S,5R,8R,9R,10R,13S,14R,15S)-13-(7-acetamidoheptylcarbamoyl)-4,9,10-trimethyl-15-propan-2-yl-3-prop-1-en-2-yl-2,3,5,6,7,8,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-4-yl]propanoic acid
  参考文献：
  名称：

  A-ring modified betulinic acid derivatives as potent cancer preventive agents

  摘要：

  Ten new 3,4-seco betulinic acid (BA) derivatives were designed and synthesized. Among them, compounds 7-15 exhibited enhanced chemopreventive ability in an in vitro short-term 12-O-tetradecanoylphorbol- 13-acetate (TPA) induced Epstein-Barr virus early antigen (EBV-EA) activation assay in Raji cells. Specifically, analogs with a free C-28 carboxylic acid, including 7, 8, 11, and 13, inhibited EBV-EA activation significantly. The most potent compound 8 displayed 100% inhibition at 1 x 10(3) mol ratio/TPA and 73.4%, 35.9%, and 8.4% inhibition at 5 x 10(2), 1 x 10(2), and 1 x 10 mol ratio/TPA, respectively, comparable with curcumin at high concentration and better than curcumin at low concentration. The potent chemopreventive activity of novel seco A-ring BAs (8 and 11) was further confirmed in an in vivo mouse skin carcinogenesis assay. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.041
• 作为产物：
  描述：

  路路通酸 在 吡啶 、 4-二甲氨基吡啶 、 草酰氯 、 palladium on activated charcoal 、 氢气 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 溶剂黄146 为溶剂， 反应 0.5h， 生成 (1R,2R,5S,8S,9R,10R,13R,14R,20R)-N-(7-acetamidoheptyl)-1,2,14,19,19-pentamethyl-17-oxo-8-propan-2-yl-18-oxapentacyclo[11.9.0.02,10.05,9.014,20]docosane-5-carboxamide
  参考文献：
  名称：

  A-ring modified betulinic acid derivatives as potent cancer preventive agents

  摘要：

  Ten new 3,4-seco betulinic acid (BA) derivatives were designed and synthesized. Among them, compounds 7-15 exhibited enhanced chemopreventive ability in an in vitro short-term 12-O-tetradecanoylphorbol- 13-acetate (TPA) induced Epstein-Barr virus early antigen (EBV-EA) activation assay in Raji cells. Specifically, analogs with a free C-28 carboxylic acid, including 7, 8, 11, and 13, inhibited EBV-EA activation significantly. The most potent compound 8 displayed 100% inhibition at 1 x 10(3) mol ratio/TPA and 73.4%, 35.9%, and 8.4% inhibition at 5 x 10(2), 1 x 10(2), and 1 x 10 mol ratio/TPA, respectively, comparable with curcumin at high concentration and better than curcumin at low concentration. The potent chemopreventive activity of novel seco A-ring BAs (8 and 11) was further confirmed in an in vivo mouse skin carcinogenesis assay. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.041