10,11-Dihydro-5-(2-hydroxyethyl)-10-hydroxy-5H-dibenzo[a,d]cyclohepten-5,10-imine | 125024-05-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 二苯并环庚烯
• 英文名称: 10,11-Dihydro-5-(2-hydroxyethyl)-10-hydroxy-5H-dibenzo[a,d]cyclohepten-5,10-imine
• 英文别名: 1-(2-Hydroxyethyl)-16-azatetracyclo[7.6.1.02,7.010,15]hexadeca-2,4,6,10,12,14-hexaen-9-ol
• CAS: 125024-05-7
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: QEJHHBSUEZXFCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  52.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  10,11-Dihydro-5-(2-hydroxyethyl)-10-hydroxy-5H-dibenzo[a,d]cyclohepten-5,10-imine 在 sodium tetrahydroborate 、 rhodium(III) chloride 作用下， 以 乙醇 为溶剂， 以31%的产率得到(5R^*,5aS^*,9aR^*,10S^*)-5a,6,7,8,9,9a,10,11-octahydro-10-hydroxy-5-(2-hydroxyethyl)-5H-dibenzocyclohepten-5,10-imine
  参考文献：
  名称：

  Structure and activity of hydrogenated derivatives of (+)-5-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine (MK-801)

  摘要：

  Several hydrogenated derivatives of the potent NMDA antagonist 1 have been prepared and evaluated as competitive inhibitors of [3H]-1 binding. These compounds were also tested for their ability to act as noncompetitive antagonists of NMDA in vitro. These studies indicate that two aromatic rings are not strictly required for high-affinity binding or NMDA antagonism.

  DOI：

  10.1021/jm00165a026
• 作为产物：
  描述：

  5-<(ethoxycarbonyl)methyl>-10-hydroxy-10,11-dihydro-5H-dibenzocyclohepten-5,10-imine 在 sodium hydroxide 作用下， 以 四氢呋喃 、 氯仿 、 水 、 氢气 为溶剂， 生成 10,11-Dihydro-5-(2-hydroxyethyl)-10-hydroxy-5H-dibenzo[a,d]cyclohepten-5,10-imine
  参考文献：
  名称：

  Derivatives of

  摘要：

  5-甲基-10,11-二氢-5H-二苯并[a,d]环庚烯-5,10-亚胺的氟代和羟基衍生物，其中取代基位于非苯环碳上，是活性的抗惊厥剂和N-甲基-D-天冬氨酸的拮抗剂。

  公开号：

  US04870079A1

文献信息

• Derivatives of 5-methyl-10,11-dihydro-5H-dibenzo-(a,d) cyclohepten-5,10-imine
  申请人：Merck & Co., Inc.

  公开号：EP0264183B1

  公开（公告）日：1992-01-15
• US4870079A
  申请人：——

  公开号：US4870079A

  公开（公告）日：1989-09-26
• Derivatives of
  申请人：Merck & Co., Inc.

  公开号：US04870079A1

  公开（公告）日：1989-09-26

  Fluoro-and hydroxy-derivatives of 5-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imines wherein the substituents are on non-benzenoid carbons are active anticonvulsants and antagonists of N-methyl-D-aspartate.

  5-甲基-10,11-二氢-5H-二苯并[a,d]环庚烯-5,10-亚胺的氟代和羟基衍生物，其中取代基位于非苯环碳上，是活性的抗惊厥剂和N-甲基-D-天冬氨酸的拮抗剂。
• Structure and activity of hydrogenated derivatives of (+)-5-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine (MK-801)
  作者：Terry A. Lyle、Catherine A. Magill、Susan F. Britcher、George H. Denny、Wayne J. Thompson、Joan S. Murphy、Antony R. Knight、John A. Kemp、George R. Marshall

  DOI：10.1021/jm00165a026

  日期：1990.3

  Several hydrogenated derivatives of the potent NMDA antagonist 1 have been prepared and evaluated as competitive inhibitors of [3H]-1 binding. These compounds were also tested for their ability to act as noncompetitive antagonists of NMDA in vitro. These studies indicate that two aromatic rings are not strictly required for high-affinity binding or NMDA antagonism.