8b,8c-dihydro-4b-methyl-4bH-azirino<2,1,3-c,d>dibenzopyrrolizine | 115878-26-7

• 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: 8b,8c-dihydro-4b-methyl-4bH-azirino<2,1,3-c,d>dibenzopyrrolizine
• 英文别名: 8b,8c-dihydro-4b-methyl-4bH-azirino<2,1,3-cd>dibenzopyrrolizine；8b,8c-dihydro-4b-methyl-4bH-azirino[2,1,3-c,d]dibenzo[a,d]pyrrolizine；9-Methyl-1-azapentacyclo[7.7.0.02,16.03,8.010,15]hexadeca-3,5,7,10,12,14-hexaene
• CAS: 115878-26-7
• 化学式: C₁₆H₁₃N
• 分子量: 219.286
• InChiKey: DMPXHCKSDMFDLM-UHFFFAOYSA-N

物化性质

• 熔点：
  112-114 °C
• 沸点：
  286.7±9.0 °C(predicted)
• 密度：
  1.31±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  8b,8c-dihydro-4b-methyl-4bH-azirino<2,1,3-c,d>dibenzopyrrolizine 在 氢氧化钾 、 sodium acetate 作用下， 以 甲醇 为溶剂， 反应 3.5h， 生成 (5R,10S,11R)-5-methyl-10,11-dihydro-5H-5,10-epiminodibenzo[a,d][7]annulen-11-ol
  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：

  5-二苯并环庚烯酮 在 二氯乙酸 、 NaO₂CH₃ 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 7.5h， 生成 8b,8c-dihydro-4b-methyl-4bH-azirino<2,1,3-c,d>dibenzopyrrolizine
  参考文献：
  名称：

  Synthesis of (5R,10S,11R)-(+)-10,11-dihydro-5-methyl-5H-dibenzo[a,d]cyclohepten-5,10-imin-11-ol: a hydroxylated metabolite of MK-0801

  摘要：

  DOI：

  10.1021/jo00288a050

文献信息

• LARSEN, ROBERT D.;DAVIS, PAUL;CORLEY, EDWARD G.;REIDER, PAUL J.;LAMANEC, +, J. ORG. CHEM., 55,(1990) N, C. 299-304
  作者：LARSEN, ROBERT D.、DAVIS, PAUL、CORLEY, EDWARD G.、REIDER, PAUL J.、LAMANEC, +

  DOI：——

  日期：——
• 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：——
• Synthesis of (5R,10S,11R)-(+)-10,11-dihydro-5-methyl-5H-dibenzo[a,d]cyclohepten-5,10-imin-11-ol: a hydroxylated metabolite of MK-0801
  作者：Robert D. Larsen、Paul Davis、Edward G. Corley、Paul J. Reider、Theresa Rothauser Lamanec、Edward J. J. Grabowski

  DOI：10.1021/jo00288a050

  日期：1990.1
• 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.