(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyl]oxy-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-carboxylic acid | 1175559-87-1

• 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: (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyl]oxy-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-carboxylic acid
• CAS: 1175559-87-1
• 化学式: C₅₂H₇₈O₄
• 分子量: 767.189
• InChiKey: WQITZAQWZLJSAZ-QHKNEDSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.2
• 重原子数：
  56
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  二十二碳六烯酸 、 白桦脂酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 吡啶 为溶剂， 生成 (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyl]oxy-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-carboxylic acid
  参考文献：
  名称：

  Cancer preventive agents 9. Betulinic acid derivatives as potent cancer chemopreventive agents

  摘要：

  C-3 esterifications of betulinic acid (BA, 1) and its A-ring homolog, ceanothic acid (CA, 2), were carried out to provide sixteen terpenoids, 4-19, including nine new compounds (4-12). All synthesized compounds were evaluated in an in vitro antitumor-promoting assay using the Epstein-Barr virus early antigen (EBVEA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells. Among them, compounds 4-6, 11-14, 16, and 17 displayed remarkable inhibitory effects of EBV-EA activation. BA analog 6, which contains a prenyl-like group, showed the most potent inhibitory effect (100%, 76%, 37%, and 11% inhibition of EBA activation at 1000, 500, 100, and 10 mol ratio/TPA, respectively, with IC50 value of 285 mol ratio/32 pmol TPA). Compound 6 merits further development as a cancer preventive agent. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.05.050

文献信息

• Cancer preventive agents 9. Betulinic acid derivatives as potent cancer chemopreventive agents
  作者：Kyoko Nakagawa-Goto、Koji Yamada、Masahiko Taniguchi、Harukuni Tokuda、Kuo-Hsiung Lee

  DOI：10.1016/j.bmcl.2009.05.050

  日期：2009.7

  C-3 esterifications of betulinic acid (BA, 1) and its A-ring homolog, ceanothic acid (CA, 2), were carried out to provide sixteen terpenoids, 4-19, including nine new compounds (4-12). All synthesized compounds were evaluated in an in vitro antitumor-promoting assay using the Epstein-Barr virus early antigen (EBVEA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells. Among them, compounds 4-6, 11-14, 16, and 17 displayed remarkable inhibitory effects of EBV-EA activation. BA analog 6, which contains a prenyl-like group, showed the most potent inhibitory effect (100%, 76%, 37%, and 11% inhibition of EBA activation at 1000, 500, 100, and 10 mol ratio/TPA, respectively, with IC50 value of 285 mol ratio/32 pmol TPA). Compound 6 merits further development as a cancer preventive agent. (C) 2009 Elsevier Ltd. All rights reserved.