11-bromo-3-chloro-5H-dibenzocyclohepten-5-one | 105176-42-9

• 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: 11-bromo-3-chloro-5H-dibenzocyclohepten-5-one
• 英文别名: 3-chloro-11-bromo-5H-dibenzo[a,d]cyclohepten-5-one；9-bromo-5-chlorotricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,9,11,13-heptaen-2-one
• CAS: 105176-42-9
• 化学式: C₁₅H₈BrClO
• 分子量: 319.585
• InChiKey: RGTBIADCDBYLQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  11-bromo-3-chloro-5H-dibenzocyclohepten-5-one 在 氯化亚砜 、 sodium borohydrid 作用下， 以 N-甲基乙酰胺 、 甲醇 、 水 、 苯 为溶剂， 生成 1-(3-chloro-11-bromo-5H-dibenzo[a,d]cyclohepten-5-yl)-4-methylpiperazine
  参考文献：
  名称：

  Pharmaceutical compositions of 4-(dibenzo-[a,d]cycloalkenyl)piperazine

  摘要：

  本发明揭示了包含4-（二苯并[a，d]环烷基）哌嗪类化合物的制药组合物，并且揭示了利用该哌嗪类化合物治疗某些心血管疾病的方法。

  公开号：

  US04616023A1
• 作为产物：
  描述：

  3-chloro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one 在 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 甲醇 、 四氯化碳 为溶剂， 反应 7.0h， 生成 11-bromo-3-chloro-5H-dibenzocyclohepten-5-one
  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

文献信息

• 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：——
• US4616023A
  申请人：——

  公开号：US4616023A

  公开（公告）日：1986-10-07
• 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.
• Pharmaceutical compositions of 4-(dibenzo-[a,d]cycloalkenyl)piperazine
  申请人：Merck & Co., Inc.

  公开号：US04616023A1

  公开（公告）日：1986-10-07

  Pharmaceutical compositions comprising 4-(dibenzo[a,d]cycloalkenyl)piperazine compounds and the use of said piperazine compounds for treatment of certain cardiovascular disorders are disclosed.

  本发明揭示了包含4-（二苯并[a，d]环烷基）哌嗪类化合物的制药组合物，并且揭示了利用该哌嗪类化合物治疗某些心血管疾病的方法。