1-benzyl-4-<2-(4-fluorophenyl)-2-hydroxyethyl>piperidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-benzyl-4-<2-(4-fluorophenyl)-2-hydroxyethyl>piperidine
• 英文别名: 1-Benzyl-4-(2'-(4''-fluorophenyl)-2'-hydroxy ethyl)-piperidine；1-Benzyl-4-(2'-(4"-fluorophenyl)-2'-hydroxy ethyl) piperidine；2-(1-Benzyl-piperidin-4-yl)-1-(4-fluoro-phenyl)-ethanol; hydrochloride；2-(1-benzylpiperidin-4-yl)-1-(4-fluorophenyl)ethanol
• 化学式: C₂₀H₂₄FNO
• 分子量: 313.415
• InChiKey: ZYRWINLYTSWVNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  草酰氯 、 二甲基亚砜 、 1-benzyl-4-<2-(4-fluorophenyl)-2-hydroxyethyl>piperidine 、 三乙胺 在 氮气 、 水 、 乙醚 、 magnesium sulfate 、 乙酸乙酯 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 1-Benzyl-4-(2'-(4''-fluorophenyl)-1'-oxoethyl)-piperidine
  参考文献：
  名称：

  N-aralkyl piperidine derivatives as psychotropic drugs

  摘要：

  提供了选择性sigma受体拮抗剂的N-芳基烷基哌嗪衍生物。这些化合物和含有它们的药物组合物可用于治疗哺乳动物中的生理或药物诱导的精神病或运动障碍。

  公开号：

  US05116846A1
• 作为产物：
  描述：

  1-苄基-4-哌啶甲醛 在 盐酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 57.58h， 生成 1-benzyl-4-<2-(4-fluorophenyl)-2-hydroxyethyl>piperidine
  参考文献：
  名称：

  Novel piperidine .sigma. receptor ligands as potential antipsychotic drugs

  摘要：

  Sigma receptor ligands represent a new class of potential antipsychotic drugs. This paper presents the structure-activity relationships leading to novel disubstituted piperidine sigma ligands, which have little or no affinity for dopamine D2 receptors. Selectivity for sigma sites over dopamine D2 or serotonin 5-HT2 receptors appears to be governed by the chemical nature of the piperidine nitrogen substituent, its distance from the basic nitrogen, and its orientation relative to the other piperidine substituent. Several of these compounds have good oral potency in some animal models used to evaluate potential antipsychotic drugs. The N-cyclopropylmethyl ketones and ethers (e.g. 6i (DuP 734), 6q, 18a, and 18n) have the best in vivo potency. Compounds 6i (DuP 734) and 6q did not cause catalepsy in the rat, even at very high doses. On the basis of the pharmacology profiles of these sigma ligands, we propose these compounds may be effective antipsychotic drugs, which do not induce extrapyramidal side effects or tardive dyskinesia.

  DOI：

  10.1021/jm00101a012

文献信息

• JPH04364164A
  申请人：——

  公开号：JPH04364164A

  公开（公告）日：1992-12-16
• US5116846A
  申请人：——

  公开号：US5116846A

  公开（公告）日：1992-05-26
• Novel piperidine .sigma. receptor ligands as potential antipsychotic drugs
  作者：Paul J. Gilligan、Gary A. Cain、Thomas E. Christos、Leonard Cook、Spencer Drummond、Alexander L. Johnson、Ahmed A. Kergaye、John F. McElroy、Kenneth W. Rohrbach

  DOI：10.1021/jm00101a012

  日期：1992.11

  Sigma receptor ligands represent a new class of potential antipsychotic drugs. This paper presents the structure-activity relationships leading to novel disubstituted piperidine sigma ligands, which have little or no affinity for dopamine D2 receptors. Selectivity for sigma sites over dopamine D2 or serotonin 5-HT2 receptors appears to be governed by the chemical nature of the piperidine nitrogen substituent, its distance from the basic nitrogen, and its orientation relative to the other piperidine substituent. Several of these compounds have good oral potency in some animal models used to evaluate potential antipsychotic drugs. The N-cyclopropylmethyl ketones and ethers (e.g. 6i (DuP 734), 6q, 18a, and 18n) have the best in vivo potency. Compounds 6i (DuP 734) and 6q did not cause catalepsy in the rat, even at very high doses. On the basis of the pharmacology profiles of these sigma ligands, we propose these compounds may be effective antipsychotic drugs, which do not induce extrapyramidal side effects or tardive dyskinesia.
• N-aralkyl piperidine derivatives as psychotropic drugs
  申请人：Du Pont Merck Pharmaceutical Company

  公开号：US05116846A1

  公开（公告）日：1992-05-26

  There are provided N-aralkyl piperidine derivatives which are selective sigma receptor antagonists. These compounds and pharmaceutical compositions containing them are useful for treating physiological or drug induced psychosis or dyskinesia in a mammal.

  提供了一些选择性sigma受体拮抗剂的N-芳基烷基哌嗪衍生物。这些化合物和含有它们的药物组合物对于治疗哺乳动物的生理或药物引起的精神病或运动障碍是有用的。