ethyl (1R,4S,5R,9S,10R,13S)-5,9,13-trimethyl-15-oxo-14-azatetracyclo[11.3.1.01,10.04,9]heptadecane-5-carboxylate | 1143506-15-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: ethyl (1R,4S,5R,9S,10R,13S)-5,9,13-trimethyl-15-oxo-14-azatetracyclo[11.3.1.01,10.04,9]heptadecane-5-carboxylate
• CAS: 1143506-15-3
• 化学式: C₂₂H₃₅NO₃
• 分子量: 361.525
• InChiKey: YWBPUBDKFRYOFK-RHSMJXSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  ethyl (4R,4aS,6aR,9S,11aR,11bS,E)-8-(hydroxyimino)-4,9,11b-trimethyltetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate 在 三氟化硼乙醚 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以77%的产率得到ethyl (1R,4S,5R,9S,10R,13S)-5,9,13-trimethyl-15-oxo-14-azatetracyclo[11.3.1.01,10.04,9]heptadecane-5-carboxylate
  参考文献：
  名称：

  Stereoselective synthesis of bioactive isosteviol derivatives as α-glucosidase inhibitors

  摘要：

  Considerable interest has been attracted in isosteviol and its derivatives because of their large variety of pharmacological activities. In this project, a series of novel compounds containing hydroxyl, hydroxymethyl group and heteroatom-containing frameworks fused with isosteviol structure were synthesized and evaluated as alpha-glucosidase inhibitors, aimed at clarifying the structure-activity correlation. The results indicated that these isosteviol derivatives were capable of inhibiting in vitro alpha-glucosidase with moderate to good activities. Among them, indole derivative 15b exhibited the highest activities and thus may be exploitable as a lead compound for the development of potent alpha-glucosidase inhibitors. (c) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2009.01.017