2-cyano-3,12-dioxooleana-1,9(11)-dien-28-onitrile

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-onitrile
• 英文别名: (4aR,6aR,6aS,6bR,8aS,12aS,14bS)-4,4,6a,6b,11,11,14b-heptamethyl-3,13-dioxo-4a,5,6,6a,7,8,9,10,12,12a-decahydropicene-2,8a-dicarbonitrile
• 化学式: C₃₁H₄₀N₂O₂
• 分子量: 472.671
• InChiKey: VKTPMWHWKXESHY-BJWRZOFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  35
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氰基-3,12-二氧代齐墩果-1,9-二烯-28-酸 在 氯化亚砜 、 草酰氯 、 氨 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-onitrile
  参考文献：
  名称：

  A novel dicyanotriterpenoid, 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-onitrile, active at picomolar concentrations for inhibition of nitric oxide production

  摘要：

  New oleanane triterpenoids with various substituents at the C-17 position of 2-evano-3,12-dioxooleana-1,9(11)dien-28-oic acid (CDDO) and methyl 2-carboxy-3,12-dioxooleana-1,9(11)-dien-28-oate were synthesized. Among them, 2-cyano-3,12-dioxooleana- 1,9(11)-dien-28-onitrile shows extremely high inhibitory activity (IC50 = 1 pM level) against production of nitric oxide induced by interferon-gamma in mouse macrophages. This potency is about 100 times and 30 times more potent than CDDO and dexamethasone, respectively. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00105-1

文献信息

• Triterpenoids and Compositions Containing the Same
  申请人：Gribble Gordon W.

  公开号：US20130303607A1

  公开（公告）日：2013-11-14

  The present invention provides triterpenoids produced from natural compounds such as oleanolic acid, ursolic acid, betulinic acid, and hederagenin.

  本发明提供了由天然化合物如熊果酸、齐墩果酸、白桦酸和铁青皂苷产生的三萜类化合物。
• METHOD FOR SYNTHESIZING 2-CYANO-3,12-DIOXOOLEAN-1, 9(11)-DIEN-28-OIC ACID METHYL ESTER AND DERIVATIVES THEREOF
  申请人：Gribble Gordon W.

  公开号：US20130303797A1

  公开（公告）日：2013-11-14

  The present invention is a method for preparing triterpenoids such as 2-cyano-3,12-dioxoolean-1,9-dien-28-methyl ester and derivatives thereof from oleanic acid, ursolic acid, betulinic acid, sumaresinolic acid or hederagenin.

  本发明是一种从齐墩果酸、熊果酸、白桦酸、苏马雷西酸或藤黄苷制备三萜类化合物如2-氰基-3,12-二氧-齐墩-1,9-二烯-28-甲酯及其衍生物的方法。
• Inhibitors and methods of use thereof
  申请人：The Trustees of Dartmouth College

  公开号：US20040002463A1

  公开（公告）日：2004-01-01

  New triterpenoid derivatives with various substituents at the C-17 position of 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid (CDDO) were synthesized. Among them, 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-onitrile (CNDDO), 1-(2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl) imidazole, 1-(2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl)-2-methylimidazole, 1-(2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl)-4-methylimidazole show extremely high inhibitory activity (IC 50 =0.01-1 pM level) against production of nitric oxide induced by interferon-&ggr; in mouse macrophages. These compounds can be used in the prevention or treatment of diseases such as cancer, Alzheimer's disease, Parkinson's disease, multiple sclerosis, rheumatoid arthritis, and other inflammatory diseases. All the new triterpenoid derivatives are more potent than previously known CDDO.

  合成了在2-氰基-3,12-二氧杂环-1,9（11）-二烯-28-羧酸（CDDO）的C-17位具有不同取代基的新三萜衍生物。其中，2-氰基-3,12-二氧杂环-1,9（11）-二烯-28-腈（CNDDO）、1-（2-氰基-3,12-二氧杂环-1,9（11）-二烯-28-酰）咪唑、1-（2-氰基-3,12-二氧杂环-1,9（11）-二烯-28-酰）-2-甲基咪唑、1-（2-氰基-3,12-二氧杂环-1,9（11）-二烯-28-酰）-4-甲基咪唑显示出极高的抑制活性（IC50=0.01-1 pM水平），可以抑制由干扰素-γ诱导的小鼠巨噬细胞产生一氧化氮。这些化合物可用于预防或治疗癌症、阿尔茨海默病、帕金森病、多发性硬化症、类风湿性关节炎和其他炎症性疾病。所有新的三萜衍生物比之前已知的CDDO更具有活性。
• TERPENOID DERIVATIVE
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP2977381A1

  公开（公告）日：2016-01-27

  It is intended to provide a novel terpenoid derivative that exhibits anti-inflammatory action and a cytoprotective action by activating the Keap1/Nrf2/ARE signaling pathway. The present invention provides terpenoid derivative A represented by the following formula (I):

  本发明的目的是提供一种新型萜类衍生物，该衍生物通过激活 Keap1/Nrf2/ARE 信号通路而具有抗炎作用和细胞保护作用。本发明提供了由下式（I）代表的萜类衍生物 A：
• Terpenoid derivatives
  申请人：Daiichi Sankyo Company, Limited

  公开号：US10253060B2

  公开（公告）日：2019-04-09

  It is intended to provide a novel terpenoid derivative that exhibits anti-inflammatory action and a cytoprotective action by activating the Keap1/Nrf2/ARE signaling pathway. The present invention provides terpenoid derivative A represented by the following formula (I):

  本发明的目的是提供一种新型萜类衍生物，该衍生物通过激活 Keap1/Nrf2/ARE 信号通路而具有抗炎作用和细胞保护作用。本发明提供了由下式（I）代表的萜类衍生物 A：