calenduladiol diacetate | 65043-59-6

• 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: calenduladiol diacetate
• 英文别名: lup-20(29)-ene-3β,16β-diol diacetate；Lup-20-en-3β,16β-diol-diacetat；Calenduladiol-diacetat；[(1R,3aS,4S,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-4-acetyloxy-3a,5a,5b,8,8,11a-hexamethyl-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-9-yl] acetate
• CAS: 65043-59-6
• 化学式: C₃₄H₅₄O₄
• 分子量: 526.8
• InChiKey: MJZROJNFQNKMMS-OLMWJSBESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  38
• 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：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  calenduladiol 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以51%的产率得到calenduladiol diacetate
  参考文献：
  名称：

  Preparation, anticholinesterase activity and molecular docking of new lupane derivatives

  摘要：

  A set of twenty one lupane derivatives (2-22) was prepared from the natural triterpenoid calenduladiol (1) by transformations on the hydroxyl groups at C-3 and C-16, and also on the isopropenyl moiety. The derivatives were tested for their inhibitory activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) and some structure-activity relationships were outlined with the aid of enzyme kinetic studies and docking modelization. The most active compound resulted to be 3,16,30-trioxolup-20(29)-ene (22), with an IC50 value of 21.5 mu M for butyrylcholinesterase, which revealed a selective inhibitor profile towards this enzyme. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.04.050

文献信息

• Preparation, anticholinesterase activity and molecular docking of new lupane derivatives
  作者：María Julia Castro、Victoria Richmond、Carmen Romero、Marta S. Maier、Ana Estévez-Braun、Ángel G. Ravelo、María Belén Faraoni、Ana Paula Murray

  DOI：10.1016/j.bmc.2014.04.050

  日期：2014.7

  A set of twenty one lupane derivatives (2-22) was prepared from the natural triterpenoid calenduladiol (1) by transformations on the hydroxyl groups at C-3 and C-16, and also on the isopropenyl moiety. The derivatives were tested for their inhibitory activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) and some structure-activity relationships were outlined with the aid of enzyme kinetic studies and docking modelization. The most active compound resulted to be 3,16,30-trioxolup-20(29)-ene (22), with an IC50 value of 21.5 mu M for butyrylcholinesterase, which revealed a selective inhibitor profile towards this enzyme. (C) 2014 Elsevier Ltd. All rights reserved.