2-(4-Fluoro-phenyl)-1-(1-{3-[2-(4-fluoro-phenyl)-[1,3]dioxolan-2-yl]-propyl}-piperidin-4-yl)-ethanone | 145021-98-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-Fluoro-phenyl)-1-(1-{3-[2-(4-fluoro-phenyl)-[1,3]dioxolan-2-yl]-propyl}-piperidin-4-yl)-ethanone
• 英文别名: 2-(4-Fluorophenyl)-1-[1-[3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl]piperidin-4-yl]ethanone
• CAS: 145021-98-3
• 化学式: C₂₅H₂₉F₂NO₃
• 分子量: 429.507
• InChiKey: YOKKIHMMMWLSLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(4-Fluoro-phenyl)-1-(1-{3-[2-(4-fluoro-phenyl)-[1,3]dioxolan-2-yl]-propyl}-piperidin-4-yl)-ethanone 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以6%的产率得到1-[4-(4-fluorophenyl)-4-oxobutyl]-4-[2-(4-fluorophenyl)-1-oxoethyl]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
• 作为产物：
  描述：

  1-(1-Benzyl-piperidin-4-yl)-2-(4-fluoro-phenyl)-ethanone; compound with (Z)-but-2-enedioic acid 在 palladium on activated charcoal ammonium formate 、 potassium carbonate 、 potassium iodide 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 24.75h， 生成 2-(4-Fluoro-phenyl)-1-(1-{3-[2-(4-fluoro-phenyl)-[1,3]dioxolan-2-yl]-propyl}-piperidin-4-yl)-ethanone
  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