(4a'S,10'S,10a'S)-6'-Methoxy-1',2',9',10'-tetrahydro-4'H,10a'H-spiro[1,3-dioxolane-2,3'-[10,4a](epiminoethano)phenanthren]-10a'-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: (4a'S,10'S,10a'S)-6'-Methoxy-1',2',9',10'-tetrahydro-4'H,10a'H-spiro[1,3-dioxolane-2,3'-[10,4a](epiminoethano)phenanthren]-10a'-ol
• 英文别名: (1'R,9'S,10'S)-4'-methoxyspiro[1,3-dioxolane-2,13'-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene]-10'-ol
• 化学式: C₁₉H₂₅NO₄
• 分子量: 331.412
• InChiKey: IMUVLRIUPLKNQH-YQVWRLOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  60
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4a'S,10'S,10a'S)-6'-Methoxy-1',2',9',10'-tetrahydro-4'H,10a'H-spiro[1,3-dioxolane-2,3'-[10,4a](epiminoethano)phenanthren]-10a'-ol 在 盐酸 作用下， 以 水 为溶剂， 反应 0.5h， 生成 (1R,9S,10S)-10-hydroxy-4-methoxy-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-13-one
  参考文献：
  名称：

  The most effective influence of 17-(3-ethoxypropyl) substituent on the binding affinity and the agonistic activity in KNT-127 derivatives, δ opioid receptor agonists

  摘要：

  We investigated the structure-activity relationship of KNT-127 (opioid delta agonist) derivatives with various 17-substituents which are different in length and size. The 17-substituent in KNT-127 derivatives exerted a great influence on the affinity and agonistic activity for the delta receptor. While the compounds with electron-donating 17-substituents showed higher affinities for the delta receptor than those with electron-withdrawing groups, KNT-127 derivatives with 17-fluoroalkyl groups (the high electron-withdrawing groups) showed high selectivities for the delta receptor among evaluated compounds. In addition, the basicity of nitrogen as well as the structure of the 17-N substituent such as the length and configuration at an asymmetric carbon atom contributed to agonist properties for the delta receptor. Thus, the analog with a 17-(3-ethoxypropyl) group showed the best selectively and potent agonistic activity for the delta receptor among KNT-127 derivatives. These findings should be useful for designing novel delta selective agonists. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.10.032