benzyloxycarbonylmethyl 3β-hydroxyolean-12-en-28-oate | 1428655-30-4

• 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: benzyloxycarbonylmethyl 3β-hydroxyolean-12-en-28-oate
• 英文别名: (2-oxo-2-phenylmethoxyethyl) (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• CAS: 1428655-30-4
• 化学式: C₃₉H₅₆O₅
• 分子量: 604.871
• InChiKey: PEFVSTWAYKHFQP-IRILJHRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  44
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyloxycarbonylmethyl 3β-hydroxyolean-12-en-28-oate 在 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 66.0h， 生成 carboxymethyl 3β-{[(S)-3-hydroxy-3-carboxy]propionyloxy}olean-12-en-28-oate
  参考文献：
  名称：

  Synthesis and cytotoxicity evaluation of oleanolic acid derivatives

  摘要：

  Twelve derivatives of oleanolic acid (1) have been synthesized and evaluated for their inhibitory activities against the growth of prostate PC3, breast MCF-7, lung A549, and gastric BGC-823 cancer cells by MU assays. Within these series of derivatives, compound 17 exhibited the most potent cytotoxicity against PC3 cell line (IC50 = 0.39 mu M) and compound 28 displayed the best activity against A549 cell line (IC50 = 0.22 mu M). SAR analysis indicates that H-donor substitution at C-3 position of oleanolic acid may be advantageous for improvement of cytotoxicity against PC3, A549 and MCF-7 cell lines. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.129
• 作为产物：
  描述：

  carboxylmethyl 3β-hydroxyolean-12-en-28-oate 、 氯化苄 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 benzyloxycarbonylmethyl 3β-hydroxyolean-12-en-28-oate
  参考文献：
  名称：

  Synthesis and cytotoxicity evaluation of oleanolic acid derivatives

  摘要：

  Twelve derivatives of oleanolic acid (1) have been synthesized and evaluated for their inhibitory activities against the growth of prostate PC3, breast MCF-7, lung A549, and gastric BGC-823 cancer cells by MU assays. Within these series of derivatives, compound 17 exhibited the most potent cytotoxicity against PC3 cell line (IC50 = 0.39 mu M) and compound 28 displayed the best activity against A549 cell line (IC50 = 0.22 mu M). SAR analysis indicates that H-donor substitution at C-3 position of oleanolic acid may be advantageous for improvement of cytotoxicity against PC3, A549 and MCF-7 cell lines. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.129