3β-acetoxy-lup-20(29)-en-28-yl-1H-triazole-1-carboxylate | 1255953-10-6

• 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-acetoxy-lup-20(29)-en-28-yl-1H-triazole-1-carboxylate
• 英文别名: 3beta-Acetoxy-lup-20(29)-en-28-yl 1H-1,2,4-triazole-1-carboxylate；[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-acetyloxy-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 1,2,4-triazole-1-carboxylate
• CAS: 1255953-10-6
• 化学式: C₃₅H₅₃N₃O₄
• 分子量: 579.824
• InChiKey: MAGRHOKCFZDFJT-HJTUWXLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  42
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  83.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N,N'-羰基二(1,2,4-三氮唑) 、 白桦脂醇-3-乙酸酯 以 四氢呋喃 为溶剂， 反应 6.0h， 以74%的产率得到3β-acetoxy-lup-20(29)-en-28-yl-1H-triazole-1-carboxylate
  参考文献：
  名称：

  Synthesis and structure–activity relationship study of novel cytotoxic carbamate and N-acylheterocyclic bearing derivatives of betulin and betulinic acid

  摘要：

  Chemical transformation studies were conducted on betulin and betulinic acid, common plant-derived lupane-type triterpenes. The concise synthesis, via a stepwise approach, of betulin and betulinic acid carbamate and N-acylheterocyclic containing derivatives is described. All new compounds, as well as betulinic acid were tested in vitro for their cytotoxic activity. Most of the compounds have shown a better cytotoxic profile than betulinic acid, including the synthesized betulin derivatives. Compounds 25 and 32 were the most promising derivatives, being up to 12-fold more potent than betulinic acid against human PC-3 cell lines (IC50 values of 1.1 and 1.8 mu M, respectively). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.085

文献信息

• Synthesis and structure–activity relationship study of novel cytotoxic carbamate and N-acylheterocyclic bearing derivatives of betulin and betulinic acid
  作者：Rita C. Santos、Jorge A.R. Salvador、Silvia Marín、Marta Cascante、João N. Moreira、Teresa C.P. Dinis

  DOI：10.1016/j.bmc.2010.04.085

  日期：2010.6.15

  Chemical transformation studies were conducted on betulin and betulinic acid, common plant-derived lupane-type triterpenes. The concise synthesis, via a stepwise approach, of betulin and betulinic acid carbamate and N-acylheterocyclic containing derivatives is described. All new compounds, as well as betulinic acid were tested in vitro for their cytotoxic activity. Most of the compounds have shown a better cytotoxic profile than betulinic acid, including the synthesized betulin derivatives. Compounds 25 and 32 were the most promising derivatives, being up to 12-fold more potent than betulinic acid against human PC-3 cell lines (IC50 values of 1.1 and 1.8 mu M, respectively). (C) 2010 Elsevier Ltd. All rights reserved.