(4aS,6aS,6bR,8aR,12aS,12bR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,13-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid methyl ester | 259526-09-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aS,6aS,6bR,8aR,12aS,12bR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,13-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid methyl ester
• 英文别名: methyl (4aS,6aR,6aS,6bR,8aR,12aS,14bS)-11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,13-dioxo-1,3,4,5,6,6a,7,8,8a,11,12,14b-dodecahydropicene-4a-carboxylate
• CAS: 259526-09-5
• 化学式: C₃₂H₄₅NO₄
• 分子量: 507.714
• InChiKey: GIQXTPCKHJSGCJ-JSHNLBSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.46
• 重原子数：
  37.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  84.23
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (4aS,6aS,6bR,8aR,12aS,12bR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,13-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid methyl ester 在 苯基氯化硒 、 lithium iodide 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 (4aS,6aS,6bR,8aR,12aS,12bR)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,13-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,12b,13,14-hexadecahydro-2H-picene-4a-carboxylic acid
  参考文献：
  名称：

  Novel synthetic oleanane triterpenoids: A series of highly active inhibitors of nitric oxide production in mouse macrophages

  摘要：

  Novel oleanane triterpenoids with modified rings A and C were designed and synthesized. Among them, methyl 2-carboxy-3,12-dioxooleana-1,9-dien-28-oate showed similar high inhibitory activity (IC50 = 0.8 nM) to 2-cyano-3,12-dioxooleana-1,9-dien-28-oic acid (CDDO), which we have synthesized previously, against production of nitric oxide induced by interferon-gamma in mouse macrophages. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00623-x
• 作为产物：
  描述：

  methyl 11-oxoisoxazolo[4,5-b]olean-12-en-28-oate 在 sodium methylate 作用下， 以 甲醇 、 乙醚 为溶剂， 以92%的产率得到(4aS,6aS,6bR,8aR,12aS,12bR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,13-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid methyl ester
  参考文献：
  名称：

  Novel synthetic oleanane triterpenoids: A series of highly active inhibitors of nitric oxide production in mouse macrophages

  摘要：

  Novel oleanane triterpenoids with modified rings A and C were designed and synthesized. Among them, methyl 2-carboxy-3,12-dioxooleana-1,9-dien-28-oate showed similar high inhibitory activity (IC50 = 0.8 nM) to 2-cyano-3,12-dioxooleana-1,9-dien-28-oic acid (CDDO), which we have synthesized previously, against production of nitric oxide induced by interferon-gamma in mouse macrophages. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00623-x