4-piperidinotetrahydro-2H-thiopyran-4-carbonitrile | 59397-53-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻烷
• 英文名称: 4-piperidinotetrahydro-2H-thiopyran-4-carbonitrile
• 英文别名: 4-piperidin-1-yl-tetrahydrothiopyran-4-carbonitrile；4-piperidino-tetrahydro-4H-thiopyran-4-carbonitrile；4-piperidin-1-ylthiane-4-carbonitrile
• CAS: 59397-53-4
• 化学式: C₁₁H₁₈N₂S
• 分子量: 210.343
• InChiKey: XNIKTAHCSRKRHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-甲基噻吩 、 4-piperidinotetrahydro-2H-thiopyran-4-carbonitrile 在 正丁基锂 、 四甲基乙二胺 、 magnesium bromide 作用下， 以 乙醚 、 正己烷 为溶剂， 以67%的产率得到N-[4-(5-methyl-thiophen-2-yl)-tetrahydro-4H-thiopyran-4-yl]-piperidine
  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
• 作为产物：
  描述：

  哌啶 、 四氢噻喃-4-酮 、 丙酮氰醇 在 异丁酰胺 、 magnesium sulfate 作用下， 反应 48.0h， 以98%的产率得到4-piperidinotetrahydro-2H-thiopyran-4-carbonitrile
  参考文献：
  名称：

  大鼠小脑中的低亲和力PCP位点不仅结合TCP样结构，而且还结合BTCP样结构。

  摘要：

  尽管这种结构缺乏多巴胺能神经，但强效多巴胺（DA）再摄取抑制剂1- [1-（2-（苯并[b]硫代苯基）环己基]哌啶（BTCP）的同源物却能够在大鼠小脑中结合结局。与先前的研究相一致的一个假设是，即使它们不与前脑中的高亲和力PCP位点结合，它们也可以与大鼠小脑中以[3H] TCP标记的低亲和力PCP位点结合。制备了1- [1-（2-（硫代苯基）环己基]哌啶（TCP）和具有修饰的芳族部分且在环己基环中具有O或S原子取代的BTCP的类似物，并在大鼠前脑和小脑膜的竞争实验中进行了测试用[3H] TCP标记，在大鼠纹状体膜中用[3H] BTCP标记。结果表明，BTCP和同源物可以与大鼠小脑中以[3H] TCP标记的低亲和力PCP位点结合，对DA转运蛋白的选择性降低。相反，某些TCP类似物对这些低亲和力位点显示出非常高的选择性。它们可能是阐明这些部位尚未发现的性质和功能的重要药理工具。

  DOI：

  10.1016/s0223-5234(00)00135-5

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。
• Effect of lowered lipophilicity on the affinity of PCP analogues for the PCP receptor and the dopamine transporter
  作者：J Hamon、J Vignon、JM Kamenka

  DOI：10.1016/0223-5234(96)85170-1

  日期：1996.1

  Oxygen and sulphur atoms were introduced in the cyclohexyl and piperidinyl moieties of the basic structures 1-(1-phenylcyclohexyl)piperidine (PCP), 1-[1-(2-thienyl)cyclohexyl]piperidine (TCP), and 1-[1-(2-benzo[b]thiophenyl)cyclohexyl]pi (BTCP) to lower their global lipophilicity. The compounds obtained were tested comparatively for their affinity for the PCP receptor labelled with [H-3]TCP and for the dopamine (DA) transporter labelled with [H-3]BTCP. Lowering the global lipophilicity in PCP and TCP series is detrimental to the affinity and selectivity for the PCP receptor. In the BTCP series lowering of the global lipophilicity is less deleterious and may, on the contrary, be a useful way of increasing selectivity for the DA transporter in some instances.
• 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
• US6342511B1
  申请人：——

  公开号：US6342511B1

  公开（公告）日：2002-01-29
• [EN] NOVEL PHENCYCLIDINE DERIVATIVES, PREPARATION METHODS AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME<br/>[FR] NOUVEAUX DERIVES DE PHENCYCLIDINES, DES PROCEDES POUR LEUR PREPARATION ET DES COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：SOCIETE DE CONSEILS DE RECHERCHES ET D'APPLICATIONS SCIENTIFIQUES (S.C.R.A.S.)

  公开号：WO1998055478A1

  公开（公告）日：1998-12-10

  (EN) The invention concerns novel phenycyclidine 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 anticonvulsant.(FR) La présente invention concerne de nouveaux dérivés de phencyclidines possédant une affinité sélective pour les récepteurs de basse affinité, des procédés pour leur préparation, des compositions pharmaceutiques les contenant et leur utilisation notamment en tant qu'agent protecteur des cellules du système nerveux central ou périphérique contre les dégénérescences aiguës ou chroniques, ou comme agent anticonvulsivant.