(-)-(5R,5aS,9aR,10R)-5a,6,7,8,9,9a,10,11-octahydro-5-methyl-5H-dibenzocyclohepten-5,10-imine | 122956-48-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (-)-(5R,5aS,9aR,10R)-5a,6,7,8,9,9a,10,11-octahydro-5-methyl-5H-dibenzocyclohepten-5,10-imine
• 英文别名: 5R,5AS,9AR,10R-5a,6,7,8,9,9a,10,11-Octahydro-5-methyl-5H-dibenzo[a,d]cyclohepten-5,10-imine；(-)-(5R,5aS,9aR,10R)-5a,6,7,8,9,9a,10,11-octahydro-5-methyl-5H-dibenzo[a,d]cyclohepten-5,10-imine；(1R,9R,10R,15S)-1-methyl-16-azatetracyclo[7.6.1.02,7.010,15]hexadeca-2,4,6-triene
• CAS: 122956-48-3；125132-92-5
• 化学式: C₁₆H₂₁N
• 分子量: 227.349
• InChiKey: COGPALBKCNFTGA-BVUBDWEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-甲基-16-氮杂四环[7.6.1.02,7.010,15]十六碳-2,4,6,10,12,14-六烯 在 sodium tetrahydroborate 、 rhodium(III) chloride 作用下， 以 乙醇 为溶剂， 以62%的产率得到(-)-(5R,5aS,9aR,10R)-5a,6,7,8,9,9a,10,11-octahydro-5-methyl-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

文献信息

• Polyhydro derivatives of dibenzocyclohexen-, dibenzocyclohepten-, and dibenzocyclooctenimines
  申请人：Merck & Co., Inc.

  公开号：EP0303421A1

  公开（公告）日：1989-02-15

  10,11-Dihydro-5H-dibenzo[a,d] cyclohepten-­5,10-imines and derivatives thereof wherein one or the other or both benzo rings are hydrogenated are active anticonvulsants and antagonists of N-methyl-D-aspartate.

  10,11-二氢-5H-二苯并[a,d]环庚烯-5,10-亚胺及其衍生物（其中一个或另一个或两个苯环被氢化）是活性抗惊厥药和 N-甲基-D-天冬氨酸拮抗剂。
• LYLE, TERRY A.;MAGILL, CATHERINE A.;BRITCHER, SUSAN F.;DENNY, GEORGE H.;T+, J. MED. CHEM., 33,(1990) N, C. 1047-1052
  作者：LYLE, TERRY A.、MAGILL, CATHERINE A.、BRITCHER, SUSAN F.、DENNY, GEORGE H.、T+

  DOI：——

  日期：——
• US4870080A
  申请人：——

  公开号：US4870080A

  公开（公告）日：1989-09-26
• 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.