5-(Azepan-1-yl)-2-oxo-7-azatricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,9,11,13-heptaene-12-carbonitrile

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 环庚三烯酮
• 英文名称: 5-(Azepan-1-yl)-2-oxo-7-azatricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,9,11,13-heptaene-12-carbonitrile
• 化学式: C₂₁H₁₉N₃O
• 分子量: 329.401
• InChiKey: XUMCHOUQUCUSIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  57
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(Azepan-1-yl)-2-oxo-7-azatricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,9,11,13-heptaene-12-carbonitrile 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.17h， 生成 5-(Azepan-1-yl)-2-hydroxy-7-azatricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,9,11,13-heptaene-12-carbonitrile
  参考文献：
  名称：

  Synthesis and evaluation of novel tricyclic benzo[4.5]cyclohepta[1.2]pyridine derivatives as NMDA/NR2B antagonists

  摘要：

  A novel series of annulated tricyclic compounds was synthesized and evaluated as NMDA/NR2B antagonists. Structure-activity development was directed towards in vitro optimization of NR2B activity and selectivity over the hERG K+ channel. Preferred compounds were subsequently evaluated for selectivity in an alpha(1)-adrenergic receptor binding counter-screen and a cell-based assay of NR2B activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.028
• 作为产物：
  描述：

  环己亚胺 、 3-chloro-5-oxo-5H-benzo[4,5]cyclohepta[1,2-b]pyridine-9-carbonitrile 在 tris-(dibenzylideneacetone)dipalladium(0) 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 5-(Azepan-1-yl)-2-oxo-7-azatricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,9,11,13-heptaene-12-carbonitrile
  参考文献：
  名称：

  Synthesis and evaluation of novel tricyclic benzo[4.5]cyclohepta[1.2]pyridine derivatives as NMDA/NR2B antagonists

  摘要：

  A novel series of annulated tricyclic compounds was synthesized and evaluated as NMDA/NR2B antagonists. Structure-activity development was directed towards in vitro optimization of NR2B activity and selectivity over the hERG K+ channel. Preferred compounds were subsequently evaluated for selectivity in an alpha(1)-adrenergic receptor binding counter-screen and a cell-based assay of NR2B activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.028

文献信息

• Synthesis and evaluation of novel tricyclic benzo[4.5]cyclohepta[1.2]pyridine derivatives as NMDA/NR2B antagonists
  作者：Charles J. McIntyre、John A. McCauley、Bohumil Bednar、Rodney A. Bednar、John W. Butcher、David A. Claremon、Michael E. Cunningham、Roger M. Freidinger、Stanley L. Gaul、Carl F. Homnick、Ken S. Koblan、Scott D. Mosser、Joseph J. Romano、Nigel J. Liverton

  DOI：10.1016/j.bmcl.2009.07.028

  日期：2009.9

  A novel series of annulated tricyclic compounds was synthesized and evaluated as NMDA/NR2B antagonists. Structure-activity development was directed towards in vitro optimization of NR2B activity and selectivity over the hERG K+ channel. Preferred compounds were subsequently evaluated for selectivity in an alpha(1)-adrenergic receptor binding counter-screen and a cell-based assay of NR2B activity. (C) 2009 Elsevier Ltd. All rights reserved.