4-（4-氯苯基）-1-（1H-吲哚-3-基甲基）-4-哌啶醇 | 81226-60-0

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 4-（4-氯苯基）-1-（1H-吲哚-3-基甲基）-4-哌啶醇
• 英文名称: 1-(indol-3-ylmethyl)-4-hydroxy-4-(p-chlorophenyl)piperidine
• 英文别名: L 741626；(±)-3-[4-(4-chlorophenyl)-4-hydroxypiperidinyl]methylindole；3-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]methyl-1H-indole；4-(4-chlorophenyl)-1-(1H-indol-3-ylmethyl)-4-piperidinol；4-(4-chlorophenyl)-1-(1H-indol-3-ylmethyl)piperidin-4-ol；3-(4-(4-chlorophenyl-4-hydroxypiperidino)methyl)indole
• CAS: 81226-60-0
• 化学式: C₂₀H₂₁ClN₂O
• 分子量: 340.853
• InChiKey: LLBLNMUONVVVPG-UHFFFAOYSA-N

物化性质

• 沸点：
  548.8±50.0 °C(Predicted)
• 密度：
  1.311±0.06 g/cm3(Predicted)
• 溶解度：
  二甲基亚砜：≥20mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  39.3
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  4-（4-氯苯基）-1-（1H-吲哚-3-基甲基）-4-哌啶醇 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 4-(4-Chlorophenyl)-1-[(1-methyl-1H-indol-3-yl)methyl]piperidin-4-ol
  参考文献：
  名称：

  Analogues of the dopamine D2 receptor antagonist L741,626: Binding, function, and SAR

  摘要：

  A series of analogues of the dopamine D2 receptor antagonist L741,626 were synthesized and evaluated for binding and function at D2 family receptor subtypes. Several analogues showed comparable binding profiles to the parent ligand, however, in general, chemical modification served to reduce D2 binding affinity and selectivity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.076
• 作为产物：
  描述：

  芦竹碱 、 4-(4-氯苯基)-4-羟基哌啶 以 甲苯 为溶剂， 以95%的产率得到4-（4-氯苯基）-1-（1H-吲哚-3-基甲基）-4-哌啶醇
  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

文献信息

• Antipsychotic piperidinomethyl-indole derivatives
  申请人：John Wyeth & Brother Limited

  公开号：US04358456A1

  公开（公告）日：1982-11-09

  The invention relates to compounds of formula II ##STR1## and their pharmaceutically acceptable salts wherein R.sup.5 represents hydrogen, acyl, lower alkyl or cycloalkyl; R.sup.6 represents hydrogen, halogen, trifluormethyl, or lower alkyl; R.sup.7 represents hydrogen, lower alkyl, hydroxy, lower alkoxy, arylloweralkoxy; R.sup.8 represents hydrogen or lower alkyl; and R.sup.9 represents hydrogen or lower alkyl. The compounds have dopamine blockade activity and may be used in the treatment of psychoses including schizophrenia.

  该发明涉及公式II的化合物及其药学上可接受的盐，其中R.sup.5代表氢、酰基、较低的烷基或环烷基；R.sup.6代表氢、卤素、三氟甲基或较低的烷基；R.sup.7代表氢、较低的烷基、羟基、较低的烷氧基、芳基较低烷氧基；R.sup.8代表氢或较低的烷基；R.sup.9代表氢或较低的烷基。这些化合物具有多巴胺阻滞活性，可用于治疗包括精神分裂症在内的精神病。
• Capture compounds, collections thereof and methods for analyzing the proteome and complex compositions
  申请人：Kõster Hubert

  公开号：US20100248264A1

  公开（公告）日：2010-09-30

  Capture compounds and collections thereof and methods using the compounds for the analysis of biomolecules are provided. In particular, collections, compounds and methods are provided for analyzing complex protein mixtures, such as the proteome. The compounds are multifunctional reagents that provide for the separation and isolation of complex protein mixtures. Automated systems for performing the methods also are provided.

  提供了捕获化合物及其集合以及使用这些化合物进行生物分子分析的方法。特别地，提供了用于分析复杂蛋白质混合物（如蛋白质组）的集合、化合物和方法。这些化合物是多功能试剂，可用于分离和分离复杂的蛋白质混合物。还提供了执行这些方法的自动化系统。
• TETRAHYDROPYRROLE COMPOUND, PREPARATION METHOD THEREFOR, PHARMACEUTICAL COMPOSITION CONTAINING SAME, AND USE THEREOF
  申请人：Mediconns (Shanghai) Biopharmaceutical Co., Ltd

  公开号：EP3733670A1

  公开（公告）日：2020-11-04

  The present invention discloses a tetrahydropyrrole compound, a preparation method therefor, a pharmaceutical composition containing the same, and a use thereof. The tetrahydropyrrole compound of the present invention is represented by general formula (I). The tetrahydropyrrole compound of the present invention has better inhibitory effects on the positive symptoms of schizophrenia, and the potency thereof is equivalent to or slightly stronger than that of the positive drug olanzapine. In addition, the compound of the present invention has dual inhibitory effects on D2 receptors and DAT receptors, and is effective for treating schizophrenia and improving negative symptoms and cognitive functions, while also reducing vertebral side effects and prolactin secretion.

  本发明公开了一种四氢吡咯化合物、其制备方法、含有该化合物的药物组合物及其用途。本发明的四氢吡咯化合物由通式（I）表示。本发明的四氢吡咯化合物对精神分裂症阳性症状有较好的抑制作用，其药效与阳性药物奥氮平相当或稍强于奥氮平。此外，本发明化合物对D2受体和DAT受体具有双重抑制作用，能有效治疗精神分裂症，改善阴性症状和认知功能，同时还能减少椎体副作用和催乳素分泌。
• Pancreatic cancer therapy and diagnosis
  申请人：Deutsches Krebsforschungszentrum Stiftung des Öffentlichenrechts

  公开号：US10420757B2

  公开（公告）日：2019-09-24

  The current disclosure relates to methods for treating pancreatic cancer or chronic pancreatitis in a subject comprising administering an antagonist of a dopamine receptor to the subject wherein the dopamine receptor is, in some specific cases dopamine receptor D2 (DRD2). The antagonist in some specific cases is an RNAi construct, an antibody, or a small molecule and in more specific cases pimozide or L-741,626. The disclosure also relates to diagnostic methods comprising the detection of the expression of DRD2 in pancreatic tissue and kits for doing the same.

  本公开涉及治疗受试者胰腺癌或慢性胰腺炎的方法，包括给受试者施用多巴胺受体拮抗剂，其中多巴胺受体在某些特定情况下是多巴胺受体D2（DRD2）。在某些特定情况下，拮抗剂是 RNAi 构建物、抗体或小分子，在更具体的情况下是匹莫齐特或 L-741,626。本公开还涉及包括检测胰腺组织中 DRD2 表达的诊断方法以及用于检测的试剂盒。
• 3-[[4-(4-Chlorophenyl)piperazin-1-yl]methyl]-1<i>H</i>-pyrrolo[2,3-<i>b</i>]pyridine:  An Antagonist with High Affinity and Selectivity for the Human Dopamine D₄ Receptor
  作者：Janusz J. Kulagowski、Howard B. Broughton、Neil R. Curtis、Ian M. Mawer、Mark P. Ridgill、Raymond Baker、Frances Emms、Stephen B. Freedman、Rosemarie Marwood、Shil Patel、Smita Patel、C. Ian Ragan、Paul D. Leeson

  DOI：10.1021/jm9600712

  日期：1996.1.1