3-[4-(3-acetylaminophenyl)piperidin-1-yl]propyl methanesulfonate | 1081112-34-6

• 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: 3-[4-(3-acetylaminophenyl)piperidin-1-yl]propyl methanesulfonate
• 英文别名: 3-[4-(3-acetamidophenyl)piperidin-1-yl]propyl Methanesulfonate
• CAS: 1081112-34-6
• 化学式: C₁₇H₂₆N₂O₄S
• 分子量: 354.47
• InChiKey: DLVQFCMSTPQRGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  84.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-[4-(3-acetylaminophenyl)piperidin-1-yl]propyl methanesulfonate 在 盐酸 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 2-(4-chlorophenyl)-1-{3-[4-(3-benzoylaminophenyl)piperidin-1-yl]propyl}-1H-benzimidazole
  参考文献：
  名称：

  Synthesis and SAR investigations of novel 2-arylbenzimidazole derivatives as melanin-concentrating hormone receptor 1 (MCH-R1) antagonists

  摘要：

  Compounds containing 2-arybenzimidazole ring systems linked to arylpiperidines were synthesized and evaluated as MCH-R1 antagonists. The results of structure-activity relationship studies led to the identification of compound 4c as a potent MCH-R1 antagonist (IC50 = 1 nM). This compound also has good metabolic stability, and favorable pharmacokinetic and brain penetration properties. However 4c was found to be potent inhibitor of the hERG potassium channel. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.099
• 作为产物：
  描述：

  N1-(3-(piperidin-4-yl)phenyl)acetamide hydrochloride 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 3-[4-(3-acetylaminophenyl)piperidin-1-yl]propyl methanesulfonate
  参考文献：
  名称：

  2-Heteroaryl Benzimidazole Derivatives as Melanin Concentrating Hormone Receptor 1 (MCH-R1) Antagonists

  摘要：

  合成了一系列新型的2-杂芳基取代的苯并咪唑衍生物，在1位含有哌啶基苯乙酰胺基团，并对其作为MCH-R1拮抗剂进行了评估。广泛的SAR研究探讨了C-2杂芳基团的影响，最终确定了2-[2-(吡啶-3-基)乙基]类似物3o，该化合物表现出极高的MCH-R1结合活性，$IC_{50}$值为1 nM。该物质3o还具有低的hERG结合活性、良好的代谢稳定性和有利的药代动力学特性。

  DOI：

  10.5012/bkcs.2013.34.8.2305

文献信息

• IMIDAZOLE DERIVATIVES HAVING ARYL PIPERIDINE SUBSTITUENT, METHOD FOR PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME
  申请人：Suh Jee Hee

  公开号：US20100145054A1

  公开（公告）日：2010-06-10

  The present invention is directed to a novel imidazole derivative having an aryl piperidine substituent of formula (I) and a method for preparation thereof, and a pharmaceutical composition containing said imidazole derivative as an active ingredient for preventing or treating a MCH (melanine-concentrating hormone)-related disease.

  本发明涉及一种具有式(I)的芳基哌啶取代基的新型咪唑衍生物及其制备方法，以及含有该咪唑衍生物作为活性成分的药物组合物，用于预防或治疗与MCH（黑色素浓集激素）相关的疾病。
• WO2008/140239
  申请人：——

  公开号：——

  公开（公告）日：——
• US8198307B2
  申请人：——

  公开号：US8198307B2

  公开（公告）日：2012-06-12
• [EN] IMIDAZOLE DERIVATIVES HAVING ARYL PIPERIDINE SUBSTITUENT, METHOD FOR PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME<br/>[FR] DÉRIVÉS D'IMIDAZOLE AVEC UN SUBSTITUANT ARYL-PIPÉRIDINE, LEUR PROCÉDÉ DE PRÉPARATION ET DES COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：KOREA RES INST CHEM TECH

  公开号：WO2008140239A1

  公开（公告）日：2008-11-20

  [EN] The present invention is directed to a novel imidazole derivative having an aryl piperidine substituent of formula (I) and a method for preparation thereof, and a pharmaceutical composition containing said imidazole derivative as an active ingredient for preventing or treating a MCH (melanine-concentrating hormone)-related disease.
  [FR] La présente invention concerne un nouveau dérivé d'imidazole avec un substituant aryl-pipéridine de formule (I) et son procédé de préparation ainsi qu'une composition pharmaceutique renfermant ledit dérivé d'imidazole en tant que principe actif destiné à la prévention ou au traitement d'une maladie liée à la MCH (hormone de concentration de la mélanine).
• Synthesis and SAR investigations of novel 2-arylbenzimidazole derivatives as melanin-concentrating hormone receptor 1 (MCH-R1) antagonists
  作者：Chae Jo Lim、Nakjeong Kim、Eun Kyoung Lee、Byung Ho Lee、Kwang-Seok Oh、Sung-eun Yoo、Kyu Yang Yi

  DOI：10.1016/j.bmcl.2011.02.099

  日期：2011.4

  Compounds containing 2-arybenzimidazole ring systems linked to arylpiperidines were synthesized and evaluated as MCH-R1 antagonists. The results of structure-activity relationship studies led to the identification of compound 4c as a potent MCH-R1 antagonist (IC50 = 1 nM). This compound also has good metabolic stability, and favorable pharmacokinetic and brain penetration properties. However 4c was found to be potent inhibitor of the hERG potassium channel. (C) 2011 Elsevier Ltd. All rights reserved.