N-(1-(naphthalen-2-ylmethyl)piperidin-4-yl)benzamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(1-(naphthalen-2-ylmethyl)piperidin-4-yl)benzamide
• 英文别名: N-[1-(naphthalen-2-ylmethyl)piperidin-4-yl]benzamide
• 化学式: C₂₃H₂₄N₂O
• 分子量: 344.456
• InChiKey: OZECHSIEHKYJND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  tert-butyl [1-(2-naphthylmethyl)piperidin-4-yl]carbamate 在 N-甲基吗啉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 N-(1-(naphthalen-2-ylmethyl)piperidin-4-yl)benzamide
  参考文献：
  名称：

  Identification of substituted 4-aminopiperidines and 3-aminopyrrolidines as potent MCH-R1 antagonists for the treatment of obesity

  摘要：

  A substituted 4-aminopiperidine was identified as showing activity in an MCH assay from an HTS effort. Subsequent structural modification of the scaffold led to the identification of a number of active MCH antagonists. 3,5-Dimethoxy-N-(1-(naphthalen-2-ylmethyl)piperidin-4-yl)benzamide (5c) was among those with the highest binding affinity to the MCH receptor (K-i = 27 nM), when variations were made at benzoyl and naphthylmethyl substitution sites from the initial HTS hit. Further optimization via piperidine ring contraction resulted in enhanced MCH activity in a 3-aminopyrrolidine series, where (R)-3,5-dimethoxy-N-(1-(naphthalen-2-ylmethyl)-pyrrolidin-3-yl)benzamide (10i) was found to be an excellent MCH antagonist (K-i = 7 nM). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.07.053

文献信息

• Identification of substituted 4-aminopiperidines and 3-aminopyrrolidines as potent MCH-R1 antagonists for the treatment of obesity
  作者：Nick Kim、Kenneth M. Meyers、Jose L. Mendez-Andino、Namal C. Warshakoon、Wei Ji、John A. Wos、Annyodile Colson、M. Chrissy Mitchell、Jan R. Davis、Beth B. Pinney、Ofer Reizes、X. Eric Hu

  DOI：10.1016/j.bmcl.2006.07.053

  日期：2006.10

  A substituted 4-aminopiperidine was identified as showing activity in an MCH assay from an HTS effort. Subsequent structural modification of the scaffold led to the identification of a number of active MCH antagonists. 3,5-Dimethoxy-N-(1-(naphthalen-2-ylmethyl)piperidin-4-yl)benzamide (5c) was among those with the highest binding affinity to the MCH receptor (K-i = 27 nM), when variations were made at benzoyl and naphthylmethyl substitution sites from the initial HTS hit. Further optimization via piperidine ring contraction resulted in enhanced MCH activity in a 3-aminopyrrolidine series, where (R)-3,5-dimethoxy-N-(1-(naphthalen-2-ylmethyl)-pyrrolidin-3-yl)benzamide (10i) was found to be an excellent MCH antagonist (K-i = 7 nM). (c) 2006 Elsevier Ltd. All rights reserved.