(3β)-3-hydroxy-N-methyl-N-methoxyolean-12-en-28-amide

• 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)-3-hydroxy-N-methyl-N-methoxyolean-12-en-28-amide
• 英文别名: (3β)-hydroxy-N-methyl-N-methoxy-olean-12-en-28-amide；(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-N-methoxy-N,2,2,6a,6b,9,9,12a-octamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxamide
• 化学式: C₃₂H₅₃NO₃
• 分子量: 499.778
• InChiKey: MRYCIPVRCRGGFV-DFHVBEEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  36
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3β)-3-hydroxy-N-methyl-N-methoxyolean-12-en-28-amide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以81%的产率得到(3β)-hydroxy-28-N-methyloxime-olean-12-en
  参考文献：
  名称：

  新糖基化合成齐墩果酸的MeON-糖苷衍生物并评价其对某些癌细胞系的细胞毒性

  摘要：

  通过新糖基化设计和合成了一系列齐墩果酸的C-3和C-28 MeON-新糖苷，作为潜在的抗增殖剂。在体外评估了它们对五种人类癌细胞系的细胞毒性：人类非小细胞肺癌细胞系（A549），人类黑素瘤细胞系（A375），人类结肠癌细胞系（HCT116），人类肝癌细胞系（HepG2 ），通过细胞计数试剂盒8（CCK-8）分析检测人乳腺腺癌细胞系（MCF-7）。齐墩果酸的大多数C-3和C-28 MeON-新糖苷对被测癌细胞表现出明显的抑制作用，并且比5-氟尿嘧啶（5-FU）对HepG2细胞更敏感。结构活性关系（SAR）分析表明，糖类型和糖的d / l构型将显着影响其对新糖苷的抗增殖活性。其中，复合8a（28 - N-甲氧基氨基油烷-β -d-葡萄糖苷）对HepG2细胞表现出最有效的抗增殖活性，IC 50值为2.1 µM。进一步的药理实验表明，化合物8a可能导致形态改变和细胞周期停滞在G0 / G1期，并诱

  DOI：

  10.3390/molecules26030772
• 作为产物：
  描述：

  齐墩果酸 3-乙酸酯 在 草酰氯 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 86.0h， 生成 (3β)-3-hydroxy-N-methyl-N-methoxyolean-12-en-28-amide
  参考文献：
  名称：

  Targeting cancer cells with oleanolic and ursolic acid derived hydroxamates

  摘要：

  Oleanolic and ursolic acid derived hydroxamates were easily obtained from their parent compounds; they were screened for their cytotoxicity applying SRB assays employing several human tumor cell lines. Low EC50 values were determined for compounds in which the nitrogen as well as the oxygen in the hydroxamic acid part still holds acidic hydrogens. Thus, ursolic acid derived compounds having at least an OH and/or NH moiety in the hydroxamate part of the molecule showed good cytotoxicity but they are significantly less selective for the tumor cells than oleanolic acid derived compounds. Good results were determined for oleanolic acid derived 7 for tumor cell lines 518A2 (melanoma, EC50 = 3.3 mu M), A2780 (ovarian carcinoma, EC50 = 3.4 mu M) and HT29 (colon adenocarcinoma, EC50 = 5.6 mu M) while being significantly less cytotoxic for fibroblasts (EC50 = 20.4 mu M). (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.12.064

文献信息

• Targeting cancer cells with oleanolic and ursolic acid derived hydroxamates
  作者：Jana Wiemann、Lucie Heller、René Csuk

  DOI：10.1016/j.bmcl.2015.12.064

  日期：2016.2

  Oleanolic and ursolic acid derived hydroxamates were easily obtained from their parent compounds; they were screened for their cytotoxicity applying SRB assays employing several human tumor cell lines. Low EC50 values were determined for compounds in which the nitrogen as well as the oxygen in the hydroxamic acid part still holds acidic hydrogens. Thus, ursolic acid derived compounds having at least an OH and/or NH moiety in the hydroxamate part of the molecule showed good cytotoxicity but they are significantly less selective for the tumor cells than oleanolic acid derived compounds. Good results were determined for oleanolic acid derived 7 for tumor cell lines 518A2 (melanoma, EC50 = 3.3 mu M), A2780 (ovarian carcinoma, EC50 = 3.4 mu M) and HT29 (colon adenocarcinoma, EC50 = 5.6 mu M) while being significantly less cytotoxic for fibroblasts (EC50 = 20.4 mu M). (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis of MeON-Glycoside Derivatives of Oleanolic Acid by Neoglycosylation and Evaluation of Their Cytotoxicity against Selected Cancer Cell Lines
  作者：Zhichao Du、Guolong Li、Xiaoyang Zhou、Jian Zhang

  DOI：10.3390/molecules26030772

  日期：——

  neoglycosylation as potential antiproliferative agents. Their cytotoxicity was evaluated in vitro against five human cancer cell lines: human non-small cell lung cancer cell line (A549), human melanoma cell line (A375), human colon cancer cell line (HCT116), human liver carcinoma cell line (HepG2), human breast adenocarcinoma cell line (MCF-7) by the Cell Counting Kit-8 (CCK-8) assay. Most of C-3 and C-28 MeON-neoglycosides

  通过新糖基化设计和合成了一系列齐墩果酸的C-3和C-28 MeON-新糖苷，作为潜在的抗增殖剂。在体外评估了它们对五种人类癌细胞系的细胞毒性：人类非小细胞肺癌细胞系（A549），人类黑素瘤细胞系（A375），人类结肠癌细胞系（HCT116），人类肝癌细胞系（HepG2 ），通过细胞计数试剂盒8（CCK-8）分析检测人乳腺腺癌细胞系（MCF-7）。齐墩果酸的大多数C-3和C-28 MeON-新糖苷对被测癌细胞表现出明显的抑制作用，并且比5-氟尿嘧啶（5-FU）对HepG2细胞更敏感。结构活性关系（SAR）分析表明，糖类型和糖的d / l构型将显着影响其对新糖苷的抗增殖活性。其中，复合8a（28 - N-甲氧基氨基油烷-β -d-葡萄糖苷）对HepG2细胞表现出最有效的抗增殖活性，IC 50值为2.1 µM。进一步的药理实验表明，化合物8a可能导致形态改变和细胞周期停滞在G0 / G1期，并诱