4-(3-methoxyphenyl)-piperidine-1-propanamine | 186185-88-6

• 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: 4-(3-methoxyphenyl)-piperidine-1-propanamine
• 英文别名: 4-(3-methoxyphenyl)-1-piperidinepropanamine；4-(3-methoxyphenyl)-1-piperdinepropanamine；4-(3-Methoxyphenyl)piperidine-1-propanamine；3-[4-(3-methoxyphenyl)piperidin-1-yl]propan-1-amine
• CAS: 186185-88-6
• 化学式: C₁₅H₂₄N₂O
• 分子量: 248.368
• InChiKey: RLKKZWJYTVWNBP-UHFFFAOYSA-N

物化性质

• 熔点：
  156-157 °C
• 沸点：
  376.2±42.0 °C(Predicted)
• 密度：
  1.020±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  38.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(3-methoxyphenyl)-piperidine-1-propanamine 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 32.0h， 生成 {3-[4-(3-Methoxy-phenyl)-piperidin-1-yl]-propyl}-methyl-amine
  参考文献：
  名称：

  Dihydropyridine neuropeptide Y Y 1 receptor antagonists 2

  摘要：

  Structure-activity studies around the urea linkage in BMS-193885 (4a) identified the cyanoguanidine moiety as an effective urea replacement in a series of dihydropyridine NPY Y-1 receptor antagonists. In comparison to urea 4a (K-i = 3.3 nM), cyanoguanidine 20 (BMS-205749) displayed similar binding potency at the Y-1 receptor (K-i = 5.1 nM) and full functional antagonism (K-b = 2.6 nM) in SK-N-MC cells. Cyanoguanidine 20 also demonstrated improved permeability properties in Caco-2 cells in comparison to urea 4a (43 vs 19 nm/s). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.016
• 作为产物：
  描述：

  4(3-Methoxyphenyl)piperidine-1-propanenitrile 在 氨 、 氢气 、 镍 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 生成 4-(3-methoxyphenyl)-piperidine-1-propanamine
  参考文献：
  名称：

  Dihydropyridine neuropeptide Y Y 1 receptor antagonists 2

  摘要：

  Structure-activity studies around the urea linkage in BMS-193885 (4a) identified the cyanoguanidine moiety as an effective urea replacement in a series of dihydropyridine NPY Y-1 receptor antagonists. In comparison to urea 4a (K-i = 3.3 nM), cyanoguanidine 20 (BMS-205749) displayed similar binding potency at the Y-1 receptor (K-i = 5.1 nM) and full functional antagonism (K-b = 2.6 nM) in SK-N-MC cells. Cyanoguanidine 20 also demonstrated improved permeability properties in Caco-2 cells in comparison to urea 4a (43 vs 19 nm/s). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.016

文献信息

• Novel Dihydropyrazine Analogues as NPY Antagonists
  作者：Sing-Yuen Sit、Yazhong Huang、Ildiko Antal-Zimanyi、Sally Ward、Graham S Poindexter

  DOI：10.1016/s0960-894x(01)00765-x

  日期：2002.2

  at the NPY-Y(1) receptors (IC(50)=4.2 nM) in SK-N-MC cells. To further expand the SAR study surrounding this dihydropyridine core structure we succeeded in synthesizing an analogous series of dihydropyrazine derivatives. This structural modification yielded compounds substantially different from the parent molecules in terms of molecular polarization and electron distribution while the overall molecular

  目前，二氢吡啶是神经肽-Y（1）（NPY-Y（1））受体拮抗剂计划中的先导化合物之一。该化合物是SK-N-MC细胞中NPY-Y（1）受体（IC（50）= 4.2 nM）处的选择性，高亲和力配体。为了进一步扩展围绕该二氢吡啶核心结构的SAR研究，我们成功合成了一系列类似的二氢吡嗪衍生物。这种结构修饰产生的化合物在分子极化和电子分布方面与母体分子基本上不同，而总体分子结构通常得以保留。因此，这种性质的改变应为我们提供有关NPY受体最佳结合要求的其他SAR信息。
• Dihydropyrazine derivatives as NPY antagonists
  申请人：Bristol-Myers Squibb Company

  公开号：US06177429B1

  公开（公告）日：2001-01-23

  The present invention provides a series of non-peptidergic antagonists of NPY comprising piperidine and piperazine derivatives of 4-phenyl-1,4-dihydropyrazines of the Formula I wherein R, R1 X, Y and Z are defined herein. As antagonists of NPY-induced feeding behavior, these compounds are expected to act as effective anorexiant agents in promoting weight loss and treating eating disorders.

  本发明提供了一系列非肽类NPY拮抗剂，包括4-苯基-1,4-二氢吡嗪的哌啶和哌嗪衍生物，其化学式为I，其中R、R1、X、Y和Z在此定义。作为NPY诱导的进食行为的拮抗剂，这些化合物预计将作为有效的厌食剂，促进减重和治疗进食障碍。
• Squarate derivatives of dihydropyridine NPY antagonists
  申请人：——

  公开号：US20010047002A1

  公开（公告）日：2001-11-29

  A series of antagonists of NPY have been synthesized and are comprised of squarate derivatives of 4-phenyl-1,4-dihydropyridines of Formula (I). 1 As antagonists of NPY-induced behavior, these compounds are expected to act as effective anorexiant agents in promoting weight loss and treating eating disorders.

  一系列NPY拮抗剂已经合成，由公式（I）的4-苯基-1,4-二氢吡啶的方酸衍生物组成。这些化合物作为NPY诱导的行为的拮抗剂，预计可作为有效的抑食剂，促进减重和治疗进食障碍。
• 4-Alkyl and 4-cycloalkyl derivatives of dihydropyridine NPY antagonists
  申请人：——

  公开号：US20010049370A1

  公开（公告）日：2001-12-06

  A series of non-peptidergic antagonists of NPY have been synthesized and are comprised of 4-alkyl and cycloalkyl derivatives of dihydropyridines of Formula I. 1 X=—NH— or a covalent bond A=alkyl, cycloalkyl As antagonists of NPY-induced behavior, these compounds are expected to act as effective anorexiant agents in promoting weight loss and treating eating disorders.

  一系列非肽类NPY拮抗剂已被合成，由公式I的二氢吡啶的4-烷基和环烷基衍生物组成，其中1X==—NH—或共价键A==烷基，环烷基。这些化合物作为NPY诱导行为的拮抗剂，预计可作为有效的食欲抑制剂，促进减重和治疗进食障碍。
• Discovery of novel, orally available benzimidazoles as melanin concentrating hormone receptor 1 (MCHR1) antagonists
  作者：Pradip K. Sasmal、Sanjita Sasmal、P. Tirumala Rao、B. Venkatesham、M. Roshaiah、Chandrasekhar Abbineni、Ish Khanna、Vikram P. Jadhav、J. Suresh、Rashmi Talwar、Syed Muzeeb、Jean-Marie Receveur、Thomas M. Frimurer、Øystein Rist、Lisbeth Elster、Thomas Högberg

  DOI：10.1016/j.bmcl.2010.07.086

  日期：2010.9

  Melanin concentrating hormone (MCH) is an important mediator of energy homeostasis and plays role in several disorders such as obesity, stress, depression and anxiety. The synthesis and biological evaluation of novel benzimidazole derivatives as MCHR1 antagonists are described. The in vivo proof of principle for weight loss with a lead compound from this series is exemplified. (c) 2010 Elsevier Ltd. All rights reserved.