methyl (4aS,6aR,6bS,8aR,12aR,14aR,14bS)-11-iodo-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,7,8,8a,14a,14b-decahydropicene-4a-carboxylate | 1198076-59-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (4aS,6aR,6bS,8aR,12aR,14aR,14bS)-11-iodo-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,7,8,8a,14a,14b-decahydropicene-4a-carboxylate
• CAS: 1198076-59-3
• 化学式: C₃₁H₄₃IO₄
• 分子量: 606.585
• InChiKey: XLQRBQGCKLUKHM-ADLQCKKRSA-N

物化性质

• 沸点：
  606.6±55.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  36
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (4aS,6aR,6bS,8aR,12aR,14aR,14bS)-11-iodo-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,7,8,8a,14a,14b-decahydropicene-4a-carboxylate 、 copper(l) cyanide 在 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以89%的产率得到甲基巴多索隆
  参考文献：
  名称：

  Efficient and Scalable Synthesis of Bardoxolone Methyl (CDDO-methyl Ester)

  摘要：

  Bardoxolone methyl (2-cyano-3,12-dioxooleane-1,9(11)-dien-28-oic acid methyl ester; CDDO-Me) (1), a synthetic oleanane triterpenoid with highly potent anti-inflammatory activity (levels below 1 nM), has completed a successful phase I clinical trial for the treatment of cancer and a successful phase II trial for the treatment of chronic kidney disease in type 2 diabetes patients. Our synthesis of bardoxolone methyl (1) proceeds In similar to 50% overall yield In five steps from oleanolic acid (2), requires only one to two chromatographic purifications, and can provide gram quantities of 1.

  DOI：

  10.1021/ol400399x
• 作为产物：
  描述：

  methyl 3-oxo-1,12-oleandien-28-oate 在 间氯过氧苯甲酸 、 吡啶 、 4-二甲氨基吡啶 、 碘 、 pyridinium hydrobromide perbromide 作用下， 以 二氯甲烷 、 四氯化碳 、 乙腈 为溶剂， 反应 42.0h， 以509 mg的产率得到methyl (4aS,6aR,6bS,8aR,12aR,14aR,14bS)-11-iodo-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,7,8,8a,14a,14b-decahydropicene-4a-carboxylate
  参考文献：
  名称：

  Efficient and Scalable Synthesis of Bardoxolone Methyl (CDDO-methyl Ester)

  摘要：

  Bardoxolone methyl (2-cyano-3,12-dioxooleane-1,9(11)-dien-28-oic acid methyl ester; CDDO-Me) (1), a synthetic oleanane triterpenoid with highly potent anti-inflammatory activity (levels below 1 nM), has completed a successful phase I clinical trial for the treatment of cancer and a successful phase II trial for the treatment of chronic kidney disease in type 2 diabetes patients. Our synthesis of bardoxolone methyl (1) proceeds In similar to 50% overall yield In five steps from oleanolic acid (2), requires only one to two chromatographic purifications, and can provide gram quantities of 1.

  DOI：

  10.1021/ol400399x

文献信息

• [EN] ANTIOXIDANT INFLAMMATION MODULATORS: NOVEL DERIVATIVES OF OLEANOLIC ACID<br/>[FR] MODULATEURS D'INFLAMMATION ANTIOXYDANT : NOUVEAUX DÉRIVÉS D'ACIDE OLÉANOLIQUE
  申请人：REATA PHARMACEUTICALS INC

  公开号：WO2009146216A3

  公开（公告）日：2010-03-18
• ANTIOXIDANT INFLAMMATION MODULATORS: NOVEL DERIVATIVES OF OLEANOLIC ACID
  申请人：Jiang Xin

  公开号：US20100048911A1

  公开（公告）日：2010-02-25

  Disclosed herein are novel oleanolic acid derivatives. Methods of preparing these compounds are also disclosed. The oleanolic acid derivatives of this invention may be used for the treatment and prevention of many diseases, including cancer, neurological disorders, inflammation, and pathologies involving oxidative stress.
• US8071632B2
  申请人：——

  公开号：US8071632B2

  公开（公告）日：2011-12-06
• US8338618B2
  申请人：——

  公开号：US8338618B2

  公开（公告）日：2012-12-25