1-[1-(2-thienyl)-cyclohexyl]-1,2,5,6-tetrahydropyridine | 111318-13-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-[1-(2-thienyl)-cyclohexyl]-1,2,5,6-tetrahydropyridine
• 英文别名: 1,2,3,6-Tetrahydro-1-[1-(2-thienyl)cyclohexyl]pyridine；1-(1-thiophen-2-ylcyclohexyl)-3,6-dihydro-2H-pyridine
• CAS: 111318-13-9
• 化学式: C₁₅H₂₁NS
• 分子量: 247.404
• InChiKey: NDTNWLZCHFUWIS-UHFFFAOYSA-N

物化性质

• 熔点：
  173-174 °C
• 沸点：
  352.1±27.0 °C(Predicted)
• 密度：
  1.109±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  31.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,2,3,6-四氢吡啶 在 盐酸 、 magnesium 作用下， 反应 14.0h， 生成 1-[1-(2-thienyl)-cyclohexyl]-1,2,5,6-tetrahydropyridine
  参考文献：
  名称：

  Synthesis, phencyclidine-like pharmacology, and antiischemic potential of meta-substituted 1-(1-phenylcyclohexyl)-1,2,3,6-tetrahydropyridines

  摘要：

  A series of 1-[1-arylcyclohexyl]-1,2,3,6-tetrahydropyridines were prepared by the reaction between 1-(1-cyanocyclohexyl)-1,2,3,6-tetrahydropyridine (1) and an appropriately substituted Grignard reagent. The resulting compounds were tested for their phencyclidine binding site affinities. Selected compounds were then tested for their ability to produce ketamine appropriate responding in monkeys and/or to show neuroprotective effects in a baby rat hypoxia/ischemia model. While it was found that binding site affinity correlated well with discriminative stimulus effects, it was found to be a poor indicator of neuroprotective efficacy within this series.

  DOI：

  10.1021/jm00170a027

文献信息

• N-(1-thienylcycloalkyl)alkenylamines for treatment of neurotoxic injury
  申请人：G.D. Searle & Co.

  公开号：EP0317953A2

  公开（公告）日：1989-05-31

  Compounds, compositions and methods of treatment are described to control brain damage associated with anoxia or ischemia which typically follows stroke, cardiac arrest or perinatal asphyxia. The treatment includes administration of an N-(1-thienylcycloalkyl)alkenylamine compound as an antagonist to inhibit excitotoxic actions at major neuronal excitatory amino acid receptor sites. Compounds of most interest are those of the formula wherein R¹ is one or more groups selected from hydrido, alkyl of one to about five carbon atoms, cycloalkyl of three to about five carbon atoms, alkenyl of two to about five carbon atoms, hydroxyl and alkoxy; wherein each of R² is one or more groups selected from hydrido, alkyl of one to about five carbon atoms, cycloalkyl of three to about five carbon atoms, alkenyl of two to about five carbon atoms, hydroxyl, oxo and alkoxy; wherein R⁵ is one or more groups selected from hydrido, alkyl of one to about five carbon atoms, cycloalkyl of three to about five carbon atoms, alkenyl of two to about five carbon atoms, hydroxyl and alkoxy; and wherein the broken line within the N-containing ring represents a double bond between any two adjacent carbon atoms involving the 3-, 4- and 5-positions of the N-containing ring.

  所述化合物、组合物和治疗方法可控制与缺氧或缺血有关的脑损伤，缺氧或缺血通常是中风、心脏骤停或围产期窒息之后的症状。治疗方法包括施用 N-（1-噻吩基环烷基）烯胺化合物作为拮抗剂，以抑制主要神经元兴奋性氨基酸受体位点的兴奋毒性作用。最令人感兴趣的化合物是那些式中 其中 R¹ 是一个或多个基团，选自氢基、一至约五个碳原子的烷基、三至约五个碳原子的环烷基、二至约五个碳原子的烯基、羟基和烷氧基；其中每个 R² 是一个或多个基团，选自氢基、一至约五个碳原子的烷基、三至约五个碳原子的环烷基、二至约五个碳原子的烯基、羟基、氧代和烷氧基；其中 R⁵是一个或多个基团，选自水rido、1 至 5 个碳原子的烷基、3 至 5 个碳原子的环烷基、2 至 5 个碳原子的烯基、羟基和烷氧基；且其中含 N 环内的断线代表涉及含 N 环的 3、4 和 5 位的任意两个相邻碳原子之间的双键。
• KIESEWETTER, DALE O.;RICE, KENNER C.;MATTSON, MARIENA V.;FINN, RONALD D., J. LABELL. COMPOUNDS AND RADIOPHARM., 26,(1989) C. 332-333
  作者：KIESEWETTER, DALE O.、RICE, KENNER C.、MATTSON, MARIENA V.、FINN, RONALD D.

  DOI：——

  日期：——
• KIESEWETTER, DALE O.;RICE, KENNER C.;MATTSON, MARIENA V.;FINN, RONALD D., J. LABELL. COMPOUNDS AND RADIOPHARM., 27,(1989) N, C. 277-286
  作者：KIESEWETTER, DALE O.、RICE, KENNER C.、MATTSON, MARIENA V.、FINN, RONALD D.

  DOI：——

  日期：——
• KAMENKA, JEAN-MARC;PRIVAT, ALAIN;CHICHEPORTICHE, ROBERT RUBIN;ROUDOUIN, G+
  作者：KAMENKA, JEAN-MARC、PRIVAT, ALAIN、CHICHEPORTICHE, ROBERT RUBIN、ROUDOUIN, G+

  DOI：——

  日期：——
• THURKAUF, ANDREW;DE, COSTA BRIAN;MATTSON, MARIENA V.;FRANCE, CHARLES P.;P+, J. MED. CHEM., 33,(1990) N, C. 2211-2215
  作者：THURKAUF, ANDREW、DE, COSTA BRIAN、MATTSON, MARIENA V.、FRANCE, CHARLES P.、P+

  DOI：——

  日期：——