1-[1-(3-hydroxymethyl-piperidino)-cyclohexan-1-yl]-carbonitrile | 131774-16-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-[1-(3-hydroxymethyl-piperidino)-cyclohexan-1-yl]-carbonitrile
• 英文别名: 1-[3-(Hydroxymethyl)piperidin-1-yl]cyclohexane-1-carbonitrile
• CAS: 131774-16-8
• 化学式: C₁₃H₂₂N₂O
• 分子量: 222.33
• InChiKey: PJZKAQCHVCTVHZ-UHFFFAOYSA-N

物化性质

• 沸点：
  353.8±22.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  47.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[1-(3-hydroxymethyl-piperidino)-cyclohexan-1-yl]-carbonitrile 在 二溴亚砜 、 magnesium 作用下， 反应 12.0h， 生成 1-[1-(1-Benzothiophen-2-yl)cyclohexyl]-3-(bromomethyl)piperidine
  参考文献：
  名称：

  Arylcyclohexylamines derived from BTCP are potent indirect catecholamine agonists

  摘要：

  N-[1-(2-Benzo[b]thiophenyl)cyclohexyl]piperidine (BTCP)-related molecules were prepared by means of chemical modulation of the 3 rings which constitute this dopamine (DA) and norepinephrine (NE) uptake inhibitor. Tested in vitro (binding to the DA uptake complex and to the PCP receptor sites, inhibition of the synaptosomal uptake of DA and NE) and in vivo (locomotor activity in mice) these molecules showed good homogeneity of action. The newly prepared structures, although formally related to the phencyclidine (PCP) structural model, no longer display significant affinity for the PCP receptor. These compounds behave like a new series of indirect potent stimulants of the dopaminergic and noradrenergic systems leading to potential antidepressive compounds.

  DOI：

  10.1016/0223-5234(93)90124-w
• 作为产物：
  描述：

  3-哌啶甲醇 、 环己酮 、 丙酮氰醇 在 异丁酰胺 、 magnesium sulfate 作用下， 以81%的产率得到1-[1-(3-hydroxymethyl-piperidino)-cyclohexan-1-yl]-carbonitrile
  参考文献：
  名称：

  The search for TCP analogues binding to the low affinity PCP receptor sites in the rat cerebellum

  摘要：

  With the aim of obtaining selective ligands of the low affinity binding sites of [H-3]-1-[1-(2-thienyl) cyclohexyl] piperidine ([H-3]TCP) in the rat cerebellum, oxygen and sulfur atoms were introduced in the TCP structure and derivatives to obtain analogues with a lowered lipophilicity. These compounds, and others already obtained, were assayed comparatively to determine their affinities for three sites labeled with [H-3]TCP: one in the forebrain, the originally described PCP receptor, and two in the rat cerebellum. Lowering the Lipophilicity and modifying the hetero-aromatic moiety yielded some Ligands with increased affinity for the low affinity sites in the rat cerebellum and decreased affinity for the high affinity sites in the forebrain. Particularly, two compounds displaying both a high affinity and a good selectivity might be valuable tools to elucidate the pharmacology of the low affinity PCP sites labeled with [H-3]TCP in the rat cerebellum. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80046-4

文献信息

• Phencyclidine derivatives, preparation method and pharmaceutical compositions containing same
  申请人：Societe de Conseils de Recherches et d'Applications Scientifiques (S.C.R.A.S.)

  公开号：US06342511B1

  公开（公告）日：2002-01-29

  The invention concerns novel phenylcyclidine derivatives with selective affinity for low affinity receptors, methods for preparing them, pharmaceutical compositions containing them and their use as protective agents for central or peripheral nervous system cells against acute or chronic degeneration, or as an anticonvulsant.

  这项发明涉及具有选择性亲和力的新型苯环丙胺衍生物，以及用于制备它们的方法、含有它们的药物组合物，以及它们作为中枢或外周神经系统细胞的保护剂对抗急性或慢性退化，或作为抗癫痫药物的用途。
• 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：——
• NOUVEAUX DERIVES DE PHENCYCLIDINES, DES PROCEDES POUR LEUR PREPARATION ET DES COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：SOCIETE DE CONSEILS DE RECHERCHESET D'APPLICATIONS SCIENTIFIQUES (S.C.R.A.S.)

  公开号：EP0986555A1

  公开（公告）日：2000-03-22
• US5248686A
  申请人：——

  公开号：US5248686A

  公开（公告）日：1993-09-28
• US6342511B1
  申请人：——

  公开号：US6342511B1

  公开（公告）日：2002-01-29