(+/-)-5-(ethoxycarbonyl)-10,11-dihydro-5H-dibenzocyclohepten-5,10-imine | 129746-25-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-5-(ethoxycarbonyl)-10,11-dihydro-5H-dibenzocyclohepten-5,10-imine
• 英文别名: 5-ethoxycarbonyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine；(+/-)-5-(ethoxycarbonyl)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine；Ethyl 16-azatetracyclo[7.6.1.02,7.010,15]hexadeca-2,4,6,10,12,14-hexaene-1-carboxylate
• CAS: 129746-25-4
• 化学式: C₁₈H₁₇NO₂
• 分子量: 279.338
• InChiKey: PRIBZUACRZRAOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 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)-10,11-dihydro-5H-dibenzocyclohepten-5,10-imine 在 氰化钠 、 氨 作用下， 以 甲醇 为溶剂， 反应 40.0h， 以78%的产率得到5-氨基羰基-10,11-二氢-5H-二苯并(a,d)环庚烯-5,10-亚胺
  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
• 作为产物：
  描述：

  (+/-)-N-<(tert-butylimino)methyl>-10,11-dihydro-5H-dibenzocyclohepten-5,10-imine 在 六甲基磷酰三胺 、 硫酸 、 仲丁基锂 作用下， 以 乙醇 为溶剂， 反应 12.5h， 生成 (+/-)-5-(ethoxycarbonyl)-10,11-dihydro-5H-dibenzocyclohepten-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

• J. Med. Chem. 1990, 33, 1069-1076
  作者：

  DOI：——

  日期：——
• 5-AMINOCARBONYL-5H-DIBENZO a,d]CYCLOHEPTEN-5,10-IMINES FOR TREATMENT OF EPILEPSY AND COCAINE ADDICTION
  申请人：THE UNITED STATES OF AMERICA as represented by the Secretary United States Department of Commerce

  公开号：EP0472526B1

  公开（公告）日：1996-05-08
• US5196415A
  申请人：——

  公开号：US5196415A

  公开（公告）日：1993-03-23
• [EN] 5-AMINOCARBONYL-5H-DIBENZO[a,d]CYCLOHEPTEN-5,10-IMINES FOR TREATMENT OF EPILEPSY AND COCAINE ADDICTION
  申请人：THE UNITED STATES OF AMERICA, as represented by THE SECRETARY, U.S. DEPARTMENT OF COMMERCE

  公开号：WO1990013297A1

  公开（公告）日：1990-11-15

  (EN) This invention is in the field of clinical neurology and relates specifically to compounds, compositions and methods for treatment of patients with generalized epilepsy or partial (symptomatic) epilepsy using compounds of formula (I). This invention also relates to compounds, compositions and methods of treatment for drug craving in patients addicted to cocaine.(FR) La présente invention, du domaine de la neurologie clinique, a trait en particulier aux composés, compositions et méthodes pour le traitement des patients souffrant d'épilepsie généralisée ou partielle (symptomatique) à l'aide des composés de la formule (I). Cette invention concerne aussi les composés, compositions et méthodes pour le traitement des patients cocaïnomanes en état de manque.
• [EN] TREATMENT OF ALCOHOL WITHDRAWAL SYMPTOMS
  申请人：NATIONAL INSTITUTES OF HEALTH

  公开号：WO1992019108A1

  公开（公告）日：1992-11-12

  (EN) This invention is directed to a method for treating alcohol abstinence (withdrawal) syndrome in mammals using compounds of formula (I). The preferred compound is 5-aminocarbonyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine.(FR) Méthode de traitement du syndrome de sevrage éthylique chez les mammifères, faisant appel à des composés de formule (I). On utilise de préférence le composé 5-aminocarbonyle-10,11-dihydro-5H-dibenzo[a,d]cycloheptène-5,10-imine.