(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-carboxylic acid ethyl ester | 443104-34-5

• 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-carboxylic acid ethyl ester
• CAS: 443104-34-5
• 化学式: C₃₂H₄₈O₄
• 分子量: 496.731
• InChiKey: WMSAXFXHLUYIBV-KGFJPKLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  36.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  60.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

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-carboxylic acid ethyl ester 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 生成 (4aR,6aS,6bR,8aS,12aS,12bR,14bS)-4,4,6a,6b,11,11,14b-Heptamethyl-3,13-dioxo-2,3,4,4a,5,6,6a,6b,7,8,9,10,11,12,12a,12b,13,14b-octadecahydro-1H-picene-2,8a-dicarboxylic acid 8a-ethyl ester 2-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 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二甲基甲酰胺 、 lithium iodide 作用下， 以 甲苯 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-carboxylic acid ethyl 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