(+/-)-5-(aminomethyl)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine | 124070-16-2

• 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-(aminomethyl)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine
• 英文别名: 10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine-5-methanamine；16-azatetracyclo[7.6.1.02,7.010,15]hexadeca-2,4,6,10,12,14-hexaen-1-ylmethanamine
• CAS: 124070-16-2
• 化学式: C₁₆H₁₆N₂
• 分子量: 236.316
• InChiKey: BPDAOPLNZXIVQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-氨基羰基-10,11-二氢-5H-二苯并(a,d)环庚烯-5,10-亚胺 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以92%的产率得到(+/-)-5-(aminomethyl)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine
  参考文献：
  名称：

  Synthesis and structure-activity relationship of C5-substituted analogs of (.+-.)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5, 10-imine [(.+-.)-desmethyl-MK801]: ligands for the NMDA receptor-coupled phencyclidine binding site

  摘要：

  A series of eight C5-substituted analogues of (+-)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine (1) have been prepared by the directed lithiation-alkylation (and acylation) of its (+-)-N-tert-butylformamidinyl derivative 2 followed by formamidine solvolysis. An additional 10 analogues were prepared by elaboration of the C5-ethyl ester derivative. Analogues possessing large (e.g. propyl and larger) lipophilic substituents displace [3H]-1-(1-thienylcyclohexyl)piperidine [( 3H]TCP) from the high-affinity phencyclidine (PCP) binding site in rat brain homogenates only at high concentrations (Ki greater than 1000 nM); however, the presence of a polar amino functionality (e.g. 2-aminoethyl) offsets this effect (Ki = 20 nM). Thus, the boundary condition for lipophilic substituents larger than ethyl appears to be polar in nature. Interaction of the 11 relatively small (MR less than 14) C5-substituted analogues of 1 with the high-affinity PCP binding site associated with the N-methyl-D-aspartate (NMDA) receptor is best described by the equation log (1/Ki) = -5.83F + 0.64 pi + 7.41 (r = 0.90).

  DOI：

  10.1021/jm00165a029

文献信息

• Synthesis and structure-activity relationship of C5-substituted analogs of (.+-.)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5, 10-imine [(.+-.)-desmethyl-MK801]: ligands for the NMDA receptor-coupled phencyclidine binding site
  作者：James A. Monn、Andrew Thurkauf、Mariena V. Mattson、Arthur E. Jacobson、Kenner C. Rice

  DOI：10.1021/jm00165a029

  日期：1990.3

  A series of eight C5-substituted analogues of (+-)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine (1) have been prepared by the directed lithiation-alkylation (and acylation) of its (+-)-N-tert-butylformamidinyl derivative 2 followed by formamidine solvolysis. An additional 10 analogues were prepared by elaboration of the C5-ethyl ester derivative. Analogues possessing large (e.g. propyl and larger) lipophilic substituents displace [3H]-1-(1-thienylcyclohexyl)piperidine [( 3H]TCP) from the high-affinity phencyclidine (PCP) binding site in rat brain homogenates only at high concentrations (Ki greater than 1000 nM); however, the presence of a polar amino functionality (e.g. 2-aminoethyl) offsets this effect (Ki = 20 nM). Thus, the boundary condition for lipophilic substituents larger than ethyl appears to be polar in nature. Interaction of the 11 relatively small (MR less than 14) C5-substituted analogues of 1 with the high-affinity PCP binding site associated with the N-methyl-D-aspartate (NMDA) receptor is best described by the equation log (1/Ki) = -5.83F + 0.64 pi + 7.41 (r = 0.90).