1-(2-Pyrrolidin-1-ylmethyl-phenyl)-piperazine | 728862-46-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-(2-Pyrrolidin-1-ylmethyl-phenyl)-piperazine
• 英文别名: 1-[2-(Pyrrolidin-1-ylmethyl)phenyl]piperazine
• CAS: 728862-46-2
• 化学式: C₁₅H₂₃N₃
• 分子量: 245.368
• InChiKey: IXVZSNAKBCEJDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  18.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-Pyrrolidin-1-ylmethyl-phenyl)-piperazine 、 Boc-D-Tic-D-p-Cl-Phe-OH 在 N-羟基-7-氮杂苯并三氮唑 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 生成 (R)-1,2,3,4-Tetrahydro-isoquinoline-3-carboxylic acid {(R)-1-(4-chloro-benzyl)-2-oxo-2-[4-(2-pyrrolidin-1-ylmethyl-phenyl)-piperazin-1-yl]-ethyl}-amide
  参考文献：
  名称：

  WO2006/133098

  摘要：

  公开号：
• 作为产物：
  描述：

  四氢吡咯 、 1-Boc-4-(2-甲酰苯基)哌嗪 在 titanium(IV) isopropylate 、 sodium tetrahydroborate 、 三氟乙酸 作用下， 生成 1-(2-Pyrrolidin-1-ylmethyl-phenyl)-piperazine
  参考文献：
  名称：

  WO2006/133098

  摘要：

  公开号：

文献信息

• Synthesis and Structure−Activity Relationships of Novel Arylpiperazines as Potent and Selective Agonists of the Melanocortin Subtype-4 Receptor
  作者：Timothy I. Richardson、Paul L. Ornstein、Karin Briner、Matthew J. Fisher、Ryan T. Backer、C. Kelly Biggers、Michael P. Clay、Paul J. Emmerson、Larry W. Hertel、Hansen M. Hsiung、Saba Husain、Steven D. Kahl、Jonathan A. Lee、Terry D. Lindstrom、Michael J. Martinelli、John P. Mayer、Jeffery T. Mullaney、Thomas P. O'Brien、Joseph M. Pawlak、Kevin D. Revell、Jikesh Shah、John M. Zgombick、R. Jason Herr、Alex Melekhov、Peter B. Sampson、Chi-Hsin R. King

  DOI：10.1021/jm0304109

  日期：2004.1.1

  The melanocortin receptors have been implicated as potential targets for a number of important therapeutic indications, including inflammation, sexual dysfunction, and obesity. We identified compound 1, an arylpiperazine attached to the dipeptide H-D-Tic-D-p-Cl-Phe-OH, as a novel melanocortin subtype-4 receptor (MC4R) agonist through iterative directed screening of nonpeptidyl G-protein-coupled receptor biased libraries. Structure-activity relationship (SAR) studies demonstrated that substitutions at the ortho position of the aryl ring improved binding and functional potency. For example, the o-isopropyl-substituted compound 29 (K-i = 720 nM) possessed 9-fold better binding affinity compared to the unsubstituted aryl ring (K-i = 6600 nM). Sulfonamide 39 (K-i = 220 nM) fills this space with a polar substituent, resulting in a further 2-fold improvement in binding affinity. The most potent compounds such as the diethylamine 44 (K-i = 60 nM) contain a basic group at this position. Basic heterocycles such as the imidazole 50 (K-i = 110 nM) were similarly effective. We also demonstrated good oral bioavailability for sulfonamide 39.
• US7291619B2
  申请人：——

  公开号：US7291619B2

  公开（公告）日：2007-11-06
• WO2006/133098
  申请人：——

  公开号：——

  公开（公告）日：——