1-((5-methoxy-1H-indol-3-yl)methyl)-4-(4-(methylthio)phenyl)piperidin-4-ol

• 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-((5-methoxy-1H-indol-3-yl)methyl)-4-(4-(methylthio)phenyl)piperidin-4-ol
• 英文别名: SV 293；1-[(5-methoxy-1H-indol-3-yl)methyl]-4-(4-methylsulfanylphenyl)piperidin-4-ol
• 化学式: C₂₂H₂₆N₂O₂S
• 分子量: 382.527
• InChiKey: LIFHVPXIKLLTMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  73.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-甲氧基芦竹碱 在 正丁基锂 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 、 正丁醇 为溶剂， 反应 5.0h， 生成 1-((5-methoxy-1H-indol-3-yl)methyl)-4-(4-(methylthio)phenyl)piperidin-4-ol
  参考文献：
  名称：

  Synthesis and characterization of selective dopamine D2 receptor antagonists

  摘要：

  A series of indole compounds have been prepared and evaluated for affinity at D-2-like dopamine receptors using stably transfected HEK cells expressing human D-2, D-3, or D-4 dopamine receptors. These compounds share structural elements with the classical D-2-like dopamine receptor antagonists, haloperidol, N-methylspiperone, and benperidol. The compounds that share structural elements with N-methylspiperone and benperidol bind non-selectively to the D-2 and D-3 dopamine receptor subtypes. However, several of the compounds structurally similar to haloperidol were found to (a) bind to the human D-2 receptor subtype with nanomolar affinity, (b) be 10- to 100-fold selective for the human D-2 receptor compared to the human D3 receptor, and (c) bind with low affinity to the human D-4 dopamine receptor subtype. Binding at sigma (sigma) receptor subtypes, sigma(1) and sigma(2), was also examined and it was found that the position of the methoxy group on the indole was pivotal in both (a) D, versus D-3 receptor selectivity and (b) affinity at sigma(1) receptors. Adenylyl cyclase studies indicate that our indole compounds with the greatest D-2 receptor selectivity are neutral antagonists at human D-2 dopamine receptor subtypes. With stably transfected HEK cells expressing human D-2 (hD(2)-HEK), these compounds (a) have no intrinsic activity and (b) attenuated quinpirole inhibition of adenylyl cyclase. The D-2 receptor selective compounds that have been identified represent unique pharmacological tools that have potential for use in studies on the relative contribution of the D-2 dopamine receptor subtypes in physiological and behavioral situations where D-2-like dopaminergic receptor involvement is indicated. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.008