3-acetoxylupa-2,20(29)-dien-28-oic acid | 866044-70-4

• 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-acetoxylupa-2,20(29)-dien-28-oic acid
• CAS: 866044-70-4
• 化学式: C₃₂H₄₈O₄
• 分子量: 496.731
• InChiKey: LMEYIKAOZPAYAT-GKMZBMDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.79
• 重原子数：
  36.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-acetoxylupa-2,20(29)-dien-28-oic acid 、 溴甲基乙酸酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 以63%的产率得到acetoxymethyl 3-acetoxylupa-2,20(29)-dien-28-oate
  参考文献：
  名称：

  Influence of esterification and modification of A-ring in a group of lupane acids on their cytotoxicity

  摘要：

  The aim of this work was to find an optimal ester group for preparation of lupane derivatives connecting high cytotoxicity with good chemical and pharmacological properties. Activities of methyl-, pivaloyloxymethyl-(Pom-), and acetoxymethyl(Acm-) esters were compared with the activity of free acids. Although the methyl- and Pom-esters were generally less active than free acids, some Acm-esters had cytotoxicity similar to or even better than the starting compounds. Cytotoxic activity was measured in five cancer cell lines. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.011
• 作为产物：
  描述：

  乙酸异丙烯酯 、 白桦脂酸 在 对甲苯磺酸 作用下， 反应 9.0h， 以55%的产率得到3-acetoxylupa-2,20(29)-dien-28-oic acid
  参考文献：
  名称：

  Influence of esterification and modification of A-ring in a group of lupane acids on their cytotoxicity

  摘要：

  The aim of this work was to find an optimal ester group for preparation of lupane derivatives connecting high cytotoxicity with good chemical and pharmacological properties. Activities of methyl-, pivaloyloxymethyl-(Pom-), and acetoxymethyl(Acm-) esters were compared with the activity of free acids. Although the methyl- and Pom-esters were generally less active than free acids, some Acm-esters had cytotoxicity similar to or even better than the starting compounds. Cytotoxic activity was measured in five cancer cell lines. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.011