(4aS,6aR,6bS,8aR,12aS,14aR,14bS)-2,2,6a,6b,9,9,12a-Heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-octadecahydro-2H-picene-4a-carbonyl chloride | 443104-41-4

• 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: (4aS,6aR,6bS,8aR,12aS,14aR,14bS)-2,2,6a,6b,9,9,12a-Heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-octadecahydro-2H-picene-4a-carbonyl chloride
• 英文别名: (4aS,6aR,6bS,8aR,12aS,14aR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,7,8,8a,11,12,14a,14b-dodecahydropicene-4a-carbonyl chloride
• CAS: 443104-41-4
• 化学式: C₃₀H₄₃ClO₃
• 分子量: 487.123
• InChiKey: GIKBNDVJLDQPOD-WKQZTKKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  34
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  51.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4aS,6aR,6bS,8aR,12aS,14aR,14bS)-2,2,6a,6b,9,9,12a-Heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-octadecahydro-2H-picene-4a-carbonyl chloride 在 氯化亚砜 、 氨 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成 (4aR,6aS,6bR,8aS,12aS,12bR,14bS)-8a-Cyano-4,4,6a,6b,11,11,14b-heptamethyl-3,13-dioxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydro-picene-2-carboxylic acid methyl ester
  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
• 作为产物：
  描述：

  3,12-二氧代齐墩果-9(11)-烯-28-酸甲酯 在 草酰氯 、 N,N-二甲基甲酰胺 、 lithium iodide 作用下， 以 二氯甲烷 为溶剂， 生成 (4aS,6aR,6bS,8aR,12aS,14aR,14bS)-2,2,6a,6b,9,9,12a-Heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-octadecahydro-2H-picene-4a-carbonyl chloride
  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

• WO2021016191A5
  申请人：——

  公开号：WO2021016191A5

  公开（公告）日：2023-07-27
• C17 POLAR-SUBSTITUTED HETEROAROMATIC SYNTHETIC TRITERPENOIDS AND METHODS OF USE THEREOF
  申请人：REATA PHARMACEUTICALS, INC.

  公开号：US20210040142A1

  公开（公告）日：2021-02-11

  Disclosed herein are compounds of the formula: wherein the variables are defined herein. Also provided are pharmaceutical compositions thereof. In some aspects, the compounds and compositions provided herein may be used as antioxidant inflammation modulators. In some aspects, the present disclosure provides methods wherein the compounds and composition described herein are used for the treatment of diseases and disorders, including those associated with inflammation and cancer.