(3S,4S,5R,8R,9R,10R,13S,14R,15S)-4-(3-methoxy-3-oxopropyl)-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]phenanthrene-13-carboxylic acid | 1550232-91-1

• 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: (3S,4S,5R,8R,9R,10R,13S,14R,15S)-4-(3-methoxy-3-oxopropyl)-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]phenanthrene-13-carboxylic acid
• CAS: 1550232-91-1
• 化学式: C₃₁H₅₀O₄
• 分子量: 486.736
• InChiKey: RHWKKLZWBBIZLH-KXOOIEQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4S,5R,8R,9R,10R,13S,14R,15S)-4-(3-methoxy-3-oxopropyl)-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]phenanthrene-13-carboxylic acid 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以82%的产率得到(3S,4S,5R,8R,9R,10R,13S,14R,15S)-4-(2-carboxyethyl)-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]phenanthrene-13-carboxylic 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 硫酸 、 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 、 溶剂黄146 为溶剂， 生成 (3S,4S,5R,8R,9R,10R,13S,14R,15S)-4-(3-methoxy-3-oxopropyl)-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]phenanthrene-13-carboxylic 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

文献信息

• A-ring modified betulinic acid derivatives as potent cancer preventive agents
  作者：Hsin-Yi Hung、Kyoko Nakagawa-Goto、Harukuni Tokuda、Akira Iida、Nobutaka Suzuki、Ibrahim D. Bori、Keduo Qian、Kuo-Hsiung Lee

  DOI：10.1016/j.bmcl.2013.12.041

  日期：2014.2

  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.