benzyloxycarbonylmethyl 3β-{4-oxo-4-[(2-sulfoethyl)amino]butyryloxy}olean-12-en-28-oate | 1428655-40-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: benzyloxycarbonylmethyl 3β-{4-oxo-4-[(2-sulfoethyl)amino]butyryloxy}olean-12-en-28-oate
• 英文别名: 2-[[4-[[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-4,4,6a,6b,11,11,14b-heptamethyl-8a-(2-oxo-2-phenylmethoxyethoxy)carbonyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4-oxobutanoyl]amino]ethanesulfonic acid
• CAS: 1428655-40-6
• 化学式: C₄₅H₆₅NO₁₀S
• 分子量: 812.078
• InChiKey: AAWXUSLDLUSKDH-CMOJMFATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  57
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  171
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  benzyloxycarbonylmethyl 3β-{4-oxo-4-[(2-sulfoethyl)amino]butyryloxy}olean-12-en-28-oate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以91%的产率得到carboxymethyl 3β-{4-oxo-4-[(2-sulfoethyl)amino]butyryloxy}olean-12-en-28-oic acid
  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：

  benzyloxycarbonylmethyl 3β-hydroxyolean-12-en-28-oate 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 吡啶 、 乙腈 为溶剂， 反应 25.0h， 生成 benzyloxycarbonylmethyl 3β-{4-oxo-4-[(2-sulfoethyl)amino]butyryloxy}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