2-cyano-3-oxolupa-1,20(29)-dien-28-oic acid anhydride | 1224698-82-1

• 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: 2-cyano-3-oxolupa-1,20(29)-dien-28-oic acid anhydride
• 英文别名: Lupane anhydride；[(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-10-cyano-5a,5b,8,8,11a-pentamethyl-9-oxo-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,11b,12,13,13a,13b-dodecahydro-1H-cyclopenta[a]chrysene-3a-carbonyl] (1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-10-cyano-5a,5b,8,8,11a-pentamethyl-9-oxo-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,11b,12,13,13a,13b-dodecahydro-1H-cyclopenta[a]chrysene-3a-carboxylate
• CAS: 1224698-82-1
• 化学式: C₆₂H₈₄N₂O₅
• 分子量: 937.359
• InChiKey: UNAPIHBVKKAFNY-LDVOWSJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.3
• 重原子数：
  69
• 可旋转键数：
  6
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  125
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-10-Cyano-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-9-oxo-1,2,3,4,5,5a,5b,6,7,7a,8,9,11a,11b,12,13,13a,13b-octadecahydro-cyclopenta[a]chrysene-3a-carbonyl chloride 、 2-cyano-1-en-3-one betulinic acid 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以14%的产率得到2-cyano-3-oxolupa-1,20(29)-dien-28-oic acid anhydride
  参考文献：
  名称：

  2-Cyano-3,10-dioxooleana-1,9(11)-dien-28-oic acid anhydride. A novel and highly potent anti-inflammatory and cytoprotective agent

  摘要：

  2-Cyano-3,10-dioxooleana-1,9(11)-dien-28-oic acid anhydride (CDDO anhydride) has been synthesized, which is the first example of an oleanane triterpenoid anhydride. CDDO anhydride shows potency similar to or higher than the corresponding acid (CDDO) in various in vitro and in vivo assays related to inflammation and carcinogenesis. Notably, preliminary phamacokinetics studies show that CDDO anhydride levels are higher than CDDO levels in mouse tissues and blood. Further evaluation of CDDO anhydride is in progress. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.02.007

文献信息

• 2-Cyano-3,10-dioxooleana-1,9(11)-dien-28-oic acid anhydride. A novel and highly potent anti-inflammatory and cytoprotective agent
  作者：Tadashi Honda、Eric M. Padegimas、Emilie David、Chitra Sundararajan、Karen T. Liby、Charlotte Williams、Michael B. Sporn、Melean Visnick

  DOI：10.1016/j.bmcl.2010.02.007

  日期：2010.4

  2-Cyano-3,10-dioxooleana-1,9(11)-dien-28-oic acid anhydride (CDDO anhydride) has been synthesized, which is the first example of an oleanane triterpenoid anhydride. CDDO anhydride shows potency similar to or higher than the corresponding acid (CDDO) in various in vitro and in vivo assays related to inflammation and carcinogenesis. Notably, preliminary phamacokinetics studies show that CDDO anhydride levels are higher than CDDO levels in mouse tissues and blood. Further evaluation of CDDO anhydride is in progress. (C) 2010 Elsevier Ltd. All rights reserved.