(3β)-lup-20(29)-en-3,28-bis-N-ethylcarbamate | 1234661-94-9

• 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)-lup-20(29)-en-3,28-bis-N-ethylcarbamate
• 英文别名: bis(ethylcarbamate)betulin；[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-(ethylcarbamoyloxy)-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-3a-yl]methyl N-ethylcarbamate
• CAS: 1234661-94-9
• 化学式: C₃₆H₆₀N₂O₄
• 分子量: 584.883
• InChiKey: VOSFIJGEMFVZIF-ZFWQOJDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  42
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  白桦脂醇 、 异氰酸乙酯 以 氯仿 为溶剂， 反应 48.0h， 以90%的产率得到(3β)-lup-20(29)-en-3,28-bis-N-ethylcarbamate
  参考文献：
  名称：

  桦木酸和桦木素的氨基甲酸酯衍生物具有选择性的细胞毒活性

  摘要：

  描述了八种新的桦木酸（1）和桦木素（2）的合成及其抗增殖活性。测试了该化合物针对十五种肿瘤细胞系的作用。研究了由活性最高的化合物9（双（乙基氨基甲酸酯）betulin）和11（28- O-乙酰基betulin的3- O-乙基氨基甲酸酯）诱导的对正常人成纤维细胞的毒性和肺癌细胞株的死亡模式。对肺癌细胞系胱天蛋白酶3活性（A549）确定为1，5（3- ø桦木酸的-ethylcarbamate），9和11。所有衍生物在微摩尔浓度下对靶肿瘤细胞系均具有剂量依赖性的抗增殖作用。DNA片段测定法中典型梯形图的出现表明，用9和11处理肺癌细胞24小时可诱导凋亡。

  DOI：

  10.1016/j.bmcl.2010.04.004

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.
• Carbamate derivatives of betulinic acid and betulin with selective cytotoxic activity
  作者：Harish Kommera、Goran N. Kaluđerović、Sebastian Dittrich、Jutta Kalbitz、Birgit Dräger、Thomas Mueller、Reinhard Paschke

  DOI：10.1016/j.bmcl.2010.04.004

  日期：2010.6

  Synthesis and antiproliferative activity of eight new derivatives of betulinic acid (1) and betulin (2) are described. The compounds were tested against fifteen tumor cell lines. The toxicity against normal human fibroblasts and the mode of cell death on lung cancer cell line induced by the most active compounds 9 (bis(ethylcarbamate)betulin) and 11 (3-O-ethylcarbamate of 28-O-acetylbetulin) was investigated

  描述了八种新的桦木酸（1）和桦木素（2）的合成及其抗增殖活性。测试了该化合物针对十五种肿瘤细胞系的作用。研究了由活性最高的化合物9（双（乙基氨基甲酸酯）betulin）和11（28- O-乙酰基betulin的3- O-乙基氨基甲酸酯）诱导的对正常人成纤维细胞的毒性和肺癌细胞株的死亡模式。对肺癌细胞系胱天蛋白酶3活性（A549）确定为1，5（3- ø桦木酸的-ethylcarbamate），9和11。所有衍生物在微摩尔浓度下对靶肿瘤细胞系均具有剂量依赖性的抗增殖作用。DNA片段测定法中典型梯形图的出现表明，用9和11处理肺癌细胞24小时可诱导凋亡。