5-<(ethoxycarbonyl)methyl>-10,11-dihydro-5H-dibenzocyclohepten-5,10-imine | 115878-14-3

• 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: 5-<(ethoxycarbonyl)methyl>-10,11-dihydro-5H-dibenzocyclohepten-5,10-imine
• 英文别名: 5-ethoxycarbonylmethyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine；Ethyl 2-(16-azatetracyclo[7.6.1.02,7.010,15]hexadeca-2,4,6,10,12,14-hexaen-1-yl)acetate
• CAS: 115878-14-3
• 化学式: C₁₉H₁₉NO₂
• 分子量: 293.365
• InChiKey: LJXAHPHHPNRJPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-<(ethoxycarbonyl)methyl>-10,11-dihydro-5H-dibenzocyclohepten-5,10-imine 在 potassium hexamethyldisilazane 、 2-(Phenylsulfonyl)-3-phenyloxaziridin 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.25h， 以85%的产率得到5(S^*)-<(R^*)-(ethoxycarbonyl)-1-hydroxymethyl>-10-(R^*),11-dihydro-5H-dibenzocyclohepten-5,10-imine
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of a series of dibenzo[a,d]cycloalkenimines as N-methyl-D-aspartate antagonists

  摘要：

  A series of 73 dibenzo[a,d]cycloalkenimines were synthesized and evaluated for their ability to displace (+)-10,11-dihydro-5-methyl-5H-dibenzo[a,d]cyclohepten-5,10-imine ([3H]-(+)-10) from its specific binding site on rat cortical membranes. A number of the more active compounds (Ki ranging from 0.006 to 0.21 microM) were evaluated for N-methyl-D-aspartate (NMDA) antagonist activity in the rat cortical slice (Kb ranging from 0.08 to 0.9 microM) and anticonvulsant activity in the mouse against NMDA induced convulsions. The ED50 values ranged from 0.22 to 7.76 mg/kg and correlated reasonably well with the Kb determination. In the dibenzo[a,d]cyclohepten-5,10-imine series, the (+)-5S,10R enantiomer displayed consistently higher levels of biological activity. While substitution at the 3-position of (+)-10 with electronegative atoms generally increased in vitro activity, a loss of potency relative to (+)-10 (MK-801) was observed in vivo for all of the compounds tested.

  DOI：

  10.1021/jm00164a052
• 作为产物：
  描述：

  10-chloro-5-<(ethoxycarbonyl)methyl>-10,11-dihydro-5H-dibenzocyclohepten-5,10-imine hydrochloride 在 锌 作用下， 以 溶剂黄146 为溶剂， 生成 5-<(ethoxycarbonyl)methyl>-10,11-dihydro-5H-dibenzocyclohepten-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：EP0264183A1

  公开（公告）日：1988-04-20

  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-亚胺的氟衍生物和羟基衍生物（其中取代基位于非苯碳原子上）是活性抗惊厥药和 N-甲基-D-天冬氨酸拮抗剂。
• THOMPSON, WAYNE J.;ANDERSON, PAUL S.;BRITCHER, SUSAN F.;LYLE, TERRY A.;TH+, J. MED. CHEM., 33,(1990) N, C. 789-808
  作者：THOMPSON, WAYNE J.、ANDERSON, PAUL S.、BRITCHER, SUSAN F.、LYLE, TERRY A.、TH+

  DOI：——

  日期：——
• 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。
• Synthesis and pharmacological evaluation of a series of dibenzo[a,d]cycloalkenimines as N-methyl-D-aspartate antagonists
  作者：Wayne J. Thompson、Paul S. Anderson、Susan F. Britcher、Terry A. Lyle、J. Eric Thies、Catherine A. Magill、Sandor L. Varga、John E. Schwering、Paulette A. Lyle

  DOI：10.1021/jm00164a052

  日期：1990.2

  A series of 73 dibenzo[a,d]cycloalkenimines were synthesized and evaluated for their ability to displace (+)-10,11-dihydro-5-methyl-5H-dibenzo[a,d]cyclohepten-5,10-imine ([3H]-(+)-10) from its specific binding site on rat cortical membranes. A number of the more active compounds (Ki ranging from 0.006 to 0.21 microM) were evaluated for N-methyl-D-aspartate (NMDA) antagonist activity in the rat cortical slice (Kb ranging from 0.08 to 0.9 microM) and anticonvulsant activity in the mouse against NMDA induced convulsions. The ED50 values ranged from 0.22 to 7.76 mg/kg and correlated reasonably well with the Kb determination. In the dibenzo[a,d]cyclohepten-5,10-imine series, the (+)-5S,10R enantiomer displayed consistently higher levels of biological activity. While substitution at the 3-position of (+)-10 with electronegative atoms generally increased in vitro activity, a loss of potency relative to (+)-10 (MK-801) was observed in vivo for all of the compounds tested.