(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 | 918937-72-1

• 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,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
• CAS: 918937-72-1
• 化学式: C₃₁H₄₂ClNO₂
• 分子量: 496.133
• InChiKey: AMLOWIJLYKBOEA-AJNNAGPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.65
• 重原子数：
  35.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  57.93
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  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 在 氨 作用下， 以 苯 为溶剂， 以74%的产率得到(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-carboxylic acid amide
  参考文献：
  名称：

  Design, synthesis, and anti-inflammatory activity both in vitro and in vivo of new betulinic acid analogues having an enone functionality in ring A

  摘要：

  Fifteen new betulinic acid analogues were designed, synthesized, and tested for anti-inflammatory activity. Many of these analogues effectively suppress nitric oxide (NO) production in RAW cells stimulated with interferon-gamma. Analogue 10 is highly and orally active in vivo for induction of the anti-inflammatory and cytoprotective enzyme, heme oxygenase-1. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.012
• 作为产物：
  描述：

  methyl (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 在 aluminum tri-bromide 、 草酰氯 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 生成 (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
  参考文献：
  名称：

  Design, synthesis, and anti-inflammatory activity both in vitro and in vivo of new betulinic acid analogues having an enone functionality in ring A

  摘要：

  Fifteen new betulinic acid analogues were designed, synthesized, and tested for anti-inflammatory activity. Many of these analogues effectively suppress nitric oxide (NO) production in RAW cells stimulated with interferon-gamma. Analogue 10 is highly and orally active in vivo for induction of the anti-inflammatory and cytoprotective enzyme, heme oxygenase-1. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.012

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.