trans-4-(4-phenylcyclohexyl)-1-(2-pyridinyl)piperazine | 1081110-73-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: trans-4-(4-phenylcyclohexyl)-1-(2-pyridinyl)piperazine
• 英文别名: cis-4-(4-Phenylcyclohexyl)-1-(2-pyridinyl)piperazine；1-(4-phenylcyclohexyl)-4-pyridin-2-ylpiperazine
• CAS: 1081110-73-7
• 化学式: C₂₁H₂₇N₃
• 分子量: 321.465
• InChiKey: FSAWWDNTYVTGLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  19.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-4-(4-phenylcyclohexyl)-1-(2-pyridinyl)piperazine 在 盐酸 作用下， 生成
  参考文献：
  名称：

  Novel 4-(4-Aryl)cyclohexyl-1-(2-pyridyl)piperazines as Δ₈−Δ₇ Sterol Isomerase (Emopamil Binding Protein) Selective Ligands with Antiproliferative Activity

  摘要：

  To find Delta(8)-Delta(7) sterol isomerase (EBP) selective ligands, various arylpiperazines previously studied and structurally related to some a receptors ligands were preliminarily screened. Consequently, a novel series of 2- or 2,6-disubstituted (CH3, CH3O, Cl, F) cis- and trans-4-(4-aryl)cyclohexyl-1-(2-pyridyl)piperazines was developed. Radioreceptor binding assays evidenced cis-19, cis-30 and cis-33 as new ligands with nanomolar affinity toward EBP site and a good selectivity relative to EBP-related a receptors. The most selective 2,6-dimethoxy derivative (cis-33) demonstrated the highest potency (EC50 = 12.9 mu M) and efficacy (70%) in inhibiting proliferation of human prostate cancer PC-3 cell line. Among the reference compounds, sigma(2) agonist 36 (PB28) reached the maximum efficacy (100%), suggesting the contribution of the sigma(2) receptor to the antiproliferative activity, This novel class of EBP inhibitors represents a valuable tool for investigating the last steps of cholesterol biosynthesis and related pathologies, as well its a starting point for developing new anticancer drugs.

  DOI：

  10.1021/jm800965b
• 作为产物：
  描述：

  1-(2-吡啶基)哌嗪 、 4-苯基环己酮 在 sodium cyanoborohydride 、 zinc(II) chloride 作用下， 以 异丙醇 为溶剂， 反应 48.0h， 以35%的产率得到trans-4-(4-phenylcyclohexyl)-1-(2-pyridinyl)piperazine
  参考文献：
  名称：

  Novel 4-(4-Aryl)cyclohexyl-1-(2-pyridyl)piperazines as Δ₈−Δ₇ Sterol Isomerase (Emopamil Binding Protein) Selective Ligands with Antiproliferative Activity

  摘要：

  To find Delta(8)-Delta(7) sterol isomerase (EBP) selective ligands, various arylpiperazines previously studied and structurally related to some a receptors ligands were preliminarily screened. Consequently, a novel series of 2- or 2,6-disubstituted (CH3, CH3O, Cl, F) cis- and trans-4-(4-aryl)cyclohexyl-1-(2-pyridyl)piperazines was developed. Radioreceptor binding assays evidenced cis-19, cis-30 and cis-33 as new ligands with nanomolar affinity toward EBP site and a good selectivity relative to EBP-related a receptors. The most selective 2,6-dimethoxy derivative (cis-33) demonstrated the highest potency (EC50 = 12.9 mu M) and efficacy (70%) in inhibiting proliferation of human prostate cancer PC-3 cell line. Among the reference compounds, sigma(2) agonist 36 (PB28) reached the maximum efficacy (100%), suggesting the contribution of the sigma(2) receptor to the antiproliferative activity, This novel class of EBP inhibitors represents a valuable tool for investigating the last steps of cholesterol biosynthesis and related pathologies, as well its a starting point for developing new anticancer drugs.

  DOI：

  10.1021/jm800965b

文献信息

• [EN] COMPOUNDS AND METHODS OF PROMOTING MYELINATION<br/>[FR] COMPOSÉS ET PROCÉDÉS DE STIMULATION DE LA MYÉLINISATION
  申请人：UNIV CASE WESTERN RESERVE

  公开号：WO2018022904A2

  公开（公告）日：2018-02-01

  A method of promoting the generation of oligodendrocytes from oligodendrocyte precursor cells by enhancing their survival and/or maturation includes administering to the cell an effective amount of an agent that enhances and/or induces accumulation of Δ8,9-unsaturated sterol intermediates of the cholesterol biosynthesis pathway in the oligodendrocyte precursor cells.