1-(4-(3-piperidin-1-yl-propoxy)benzyl)piperidin-4-ol | 398473-38-6

• 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-(4-(3-piperidin-1-yl-propoxy)benzyl)piperidin-4-ol
• 英文别名: 1-[[4-[3-(1-Piperidinyl)propoxy]phenyl]methyl]-4-piperidinol；1-[[4-(3-piperidin-1-ylpropoxy)phenyl]methyl]piperidin-4-ol
• CAS: 398473-38-6
• 化学式: C₂₀H₃₂N₂O₂
• 分子量: 332.486
• InChiKey: OZHWKCSDZSJHKE-UHFFFAOYSA-N

物化性质

• 沸点：
  490.5±40.0 °C(Predicted)
• 密度：
  1.095±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  35.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲基磺酰氯 、 1-(4-(3-piperidin-1-yl-propoxy)benzyl)piperidin-4-ol 以 二氯甲烷 为溶剂， 生成 ST-928
  参考文献：
  名称：

  Fluorinated non-imidazole histamine H3 receptor antagonists

  摘要：

  Fluorine substituents have become a widespread and important component in drug design and development. Here, the synthesis of fluorine containing compounds and some corresponding precursor molecules are presented for potential isotope labelling as well as their data obtained with in vitro and in vivo screenings. The compounds vary in the basic centres (piperidine or pyrrolidine) and are fluoro substituted in different positions of the basic alicyclic moiety. Pharmacological evaluation resulted in ligands with high affinities at hH(3) receptor in the nanomolar and subnanomolar concentration range and some with high antagonist in vivo potencies. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.110
• 作为产物：
  描述：

  4-(3-氯丙氧基)苯甲醛 在 三乙酰氧基硼氢化钠 、 sodium carbonate 、 溶剂黄146 、 potassium iodide 作用下， 以 1,2-二氯乙烷 、 正丁醇 为溶剂， 反应 36.0h， 生成 1-(4-(3-piperidin-1-yl-propoxy)benzyl)piperidin-4-ol
  参考文献：
  名称：

  一类新的基于二胺的人类组胺H3受体拮抗剂：4-（氨基烷氧基）苄胺。

  摘要：

  制备了4-（氨基烷氧基）苄胺，并筛选了对人组胺H（3）受体的体外活性。该系列的某些成员表现出亚纳摩尔的结合亲和力。其中一个氮原子被次甲基取代的类似物显示结合亲和力大大降低。发现该系列的六个成员是人类组胺H（3）受体激活的基于细胞的模型中的拮抗剂。该系列的一个成员1- [4-（3-哌啶-1-基丙氧基）苄基]哌啶（7b）被发现是一种选择性且有效的人H（3）受体拮抗剂。

  DOI：

  10.1021/jm030185v

文献信息

• Non-imidazole aryloxyalkylamines
  申请人：——

  公开号：US20020065278A1

  公开（公告）日：2002-05-30

  Substituted aryloxyalkylamines of formula (I), compositions containing them, and methods of making and using them to treat histamine-mediated conditions.

  式(I)的取代的芳氧基烷胺，包含它们的组合物，以及使用它们治疗组胺介导的疾病的方法。
• NON-IMIDAZOLE ARYLOXYALKYLAMINES
  申请人：Apodaca Richard

  公开号：US20100004241A1

  公开（公告）日：2010-01-07

  Substituted aryloxyalkylamines of formula (I), compositions containing them, and methods of making and using them to treat histamine-mediated conditions.

  公式（I）中的取代芳氧基烷胺，包含它们的组合物，以及使用它们治疗组胺介导的疾病的制备和使用方法。
• Benzylpiperidine variations on histamine H3 receptor ligands for improved drug-likeness
  作者：Kerstin Wingen、J. Stephan Schwed、Kathleen Isensee、Lilia Weizel、Aleksandra Živković、Dalibor Odazic、Holger Stark

  DOI：10.1016/j.bmcl.2014.03.098

  日期：2014.5

  Several hH(3)R antagonists/inverse agonists entered clinical phases for a broad spectrum of mainly centrally occurring diseases. Nevertheless, many promising candidates failed due to their pharmacokinetic profile, mostly because of their strong lipophilicity and their dibasic character. Analysis of previously, as potential PET ligands synthesized compounds (ST-889, ST-928) revealed promising results concerning physicochemical properties and drug-likeness. Herein, the synthesis, the evaluation of the binding properties at the hH3R and the estimation of different physicochemical and drug-likeness properties of further novel benzylpiperidine variations on H3R antagonists is described. Due to the introduction of various small hydrophilic moieties in the structure, drug-likeness parameters have been improved. For instance, compound 12 (ST-1032) showed in addition to high affinity at the H3R (pK(i) (hH(3)R) = 9.3) clogS, clogP, LE, LipE, and LELP values of -2.48, 2.18, 0.44, 7.14, and 4.95, respectively. Also, the keto derivative 5 (ST-1703, pKi (hH(3)R) = 8.6) revealed LipE and LELP values of 5.25 and 6.84, respectively. (C) 2014 Elsevier Ltd. All rights reserved.
• NON-IMIDAZOLE ARYLOXYALKYLAMINES AS H3 RECEPTOR LIGANDS
  申请人：Ortho McNeil Pharmaceuticals, Inc.

  公开号：EP1313721A2

  公开（公告）日：2003-05-28
• US7186732B2
  申请人：——

  公开号：US7186732B2

  公开（公告）日：2007-03-06