(3β) methyl 3-hydroxy-11-oxo-olean-12-en-28-oate | 1558053-87-4

• 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: (3β) methyl 3-hydroxy-11-oxo-olean-12-en-28-oate
• 英文别名: methyl (4aS,6aR,6aS,6bR,8aR,10S,12aS,14bS)-10,14-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-4a-carboxylate
• CAS: 1558053-87-4
• 化学式: C₃₁H₄₈O₅
• 分子量: 500.719
• InChiKey: KWBZWKISOAYWPQ-GYXAIYAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  36
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (3β) methyl 3-hydroxy-12-oxo-olean-28-oate 在 potassium dichromate 、 N-羟基丁二酰亚胺 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 反应 48.0h， 以71%的产率得到(3β) methyl 3-hydroxy-11-oxo-olean-12-en-28-oate
  参考文献：
  名称：

  The chemical and biological potential of C ring modified triterpenoids

  摘要：

  A convenient and elegant route has been developed to separate the natural regioisomers triterpenoids ursolic acid (UA) and oleanolic acid (OA) as well as derivatives thereof. Eleven unknown derivatives of OA were designed, synthesized, and their cytotoxicity was investigated. Further sixteen compounds were prepared to correlate all compounds in a SAR study. It could be shown that C-ring modifications of OA and UA have only a moderate influence onto the cytotoxic activity of the compounds but a significant impact onto the ability to trigger apoptosis in ovarian cancer cells (cell line A2780). (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.11.025

文献信息

• The chemical and biological potential of C ring modified triterpenoids
  作者：Bianka Siewert、Jana Wiemann、Alexander Köwitsch、René Csuk

  DOI：10.1016/j.ejmech.2013.11.025

  日期：2014.1

  A convenient and elegant route has been developed to separate the natural regioisomers triterpenoids ursolic acid (UA) and oleanolic acid (OA) as well as derivatives thereof. Eleven unknown derivatives of OA were designed, synthesized, and their cytotoxicity was investigated. Further sixteen compounds were prepared to correlate all compounds in a SAR study. It could be shown that C-ring modifications of OA and UA have only a moderate influence onto the cytotoxic activity of the compounds but a significant impact onto the ability to trigger apoptosis in ovarian cancer cells (cell line A2780). (C) 2013 Elsevier Masson SAS. All rights reserved.