3-oxo-lup-20(29)-en-28-N-ethylcarbamate

• 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: 3-oxo-lup-20(29)-en-28-N-ethylcarbamate
• 英文别名: [(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-9-oxo-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysen-3a-yl]methyl N-ethylcarbamate
• 化学式: C₃₃H₅₃NO₃
• 分子量: 511.789
• InChiKey: NJUWCWLYTRTVQD-FZNYPPOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  37
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  28-acetoxybetulin 在 chromium(VI) oxide 、 硫酸 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 为溶剂， 反应 19.67h， 生成 3-oxo-lup-20(29)-en-28-N-ethylcarbamate
  参考文献：
  名称：

  Betulinic acid derived hydroxamates and betulin derived carbamates are interesting scaffolds for the synthesis of novel cytotoxic compounds

  摘要：

  The betulinic acid-derived hydroxamates 5-18, the amides 19-24, and betulin-derived bis-carbamates 25-28 as well as the carbamates 31-40 and 44-48 were prepared and evaluated for their anti-proliferative activity in a photometric sulforhodamine B (SRB) assay against several human cancer cell lines and nonmalignant mouse fibroblasts (NIH 3T3). While for 3-O-acetyl hydroxamic acid 5 EC50 values as low as EC50 = 1.3 mu M were found, N,O-bis-alkyl substituted hydroxamates showed lowered cytotoxicity (EC50 = 16-20 mu M). In general, hydroxamic acid derivatives showed only reduced selectivity for tumor cells, except for allyl substituted compound 13 (EC50 = 5.9 mu M for A2780 human ovarian carcinoma cells and EC50 > 30 mu M for nonmalignant mouse fibroblasts). The cytotoxicity of betulinic acid derived amides 19-24 and of betulin derived bis-carbamates 25-28 was low, except for N-ethyl substituted 25. Hexyl substituted 39 showed EC50 = 5.6 mu M (518A2 cells) while for mouse fibroblasts EC50 > 30 was determined. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.10.043

文献信息

• Betulinic acid derived hydroxamates and betulin derived carbamates are interesting scaffolds for the synthesis of novel cytotoxic compounds
  作者：Jana Wiemann、Lucie Heller、Vincent Perl、Ralph Kluge、Dieter Ströhl、René Csuk

  DOI：10.1016/j.ejmech.2015.10.043

  日期：2015.12

  The betulinic acid-derived hydroxamates 5-18, the amides 19-24, and betulin-derived bis-carbamates 25-28 as well as the carbamates 31-40 and 44-48 were prepared and evaluated for their anti-proliferative activity in a photometric sulforhodamine B (SRB) assay against several human cancer cell lines and nonmalignant mouse fibroblasts (NIH 3T3). While for 3-O-acetyl hydroxamic acid 5 EC50 values as low as EC50 = 1.3 mu M were found, N,O-bis-alkyl substituted hydroxamates showed lowered cytotoxicity (EC50 = 16-20 mu M). In general, hydroxamic acid derivatives showed only reduced selectivity for tumor cells, except for allyl substituted compound 13 (EC50 = 5.9 mu M for A2780 human ovarian carcinoma cells and EC50 > 30 mu M for nonmalignant mouse fibroblasts). The cytotoxicity of betulinic acid derived amides 19-24 and of betulin derived bis-carbamates 25-28 was low, except for N-ethyl substituted 25. Hexyl substituted 39 showed EC50 = 5.6 mu M (518A2 cells) while for mouse fibroblasts EC50 > 30 was determined. (C) 2015 Elsevier Masson SAS. All rights reserved.