naphthalene-1-sulfonic acid {trans-4-[(4-aminoquinazolin-2-ylamino)methyl]cyclohexylmethyl}amide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: naphthalene-1-sulfonic acid {trans-4-[(4-aminoquinazolin-2-ylamino)methyl]cyclohexylmethyl}amide
• 英文别名: naphthalene-1-sulfonic acid {trans-4-[(4-aminoquinazolin-2-ylamino)methyl]cyclohexylmethy}amide；N-[[trans-4-[[(4-amino-2-quinazolinyl)amino]methyl]cyclohexyl]methyl]-1-naphthalenesulfonamide；CGP 71683A
• 化学式: C₂₆H₂₉N₅O₂S
• 分子量: 475.615
• InChiKey: UULIGRNKXHCLQN-WGSAOQKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.56
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  110.0
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  tranexamic acid 在 ammonium hydroxide 、 sodium hydroxide 、 硼烷四氢呋喃络合物 、 三乙胺 作用下， 以 四氢呋喃 、 异戊醇 为溶剂， 生成 naphthalene-1-sulfonic acid {trans-4-[(4-aminoquinazolin-2-ylamino)methyl]cyclohexylmethyl}amide
  参考文献：
  名称：

  Design, synthesis and SAR of a series of 2-substituted 4-amino-quinazoline neuropeptide Y Y 5 receptor antagonists

  摘要：

  The design of a novel series of NPY-Y-5 receptor antagonists is described. Key elements for the design were the identification of weak Y-5 hits from a Y-1 program, results from a combinatorial approach and database mining. This led to the discovery of the quinazoline 4 and the aryl-sulphonamide moiety as major components of the pharmacophore for Y-5 affinity. The synthesis and SAR towards CGP71683A is described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00177-3

文献信息

• Preparation of Fluorescent Nonpeptidic Neuropeptide Y Receptor Ligands: Analogues of the Quinazoline-type Anti-obesity Y5 Antagonist CGP 71683A
  作者：Liantao Li、Matthias Mayer、Erich Schneider、Elvira Schreiber、Günther Bernhardt、Shiqi Peng、Armin Buschauer

  DOI：10.1002/ardp.200300813

  日期：2003.12

  G‐protein coupled receptors (GPCRs) and their ligands the preparation of low molecular weight fluorescence‐labelled neuropeptide Y (NPY) Y5 antagonists is reported. The naphthylsulfonyl group in the potent quinazoline‐type NPY Y5 receptor antagonist CGP 71683A was replaced with a dansyl, nitrobenzoxadiazole (NBD) or acridine‐9‐carbonyl group. In radioligand binding studies on human Y5 receptor expressing

  作为开发基于荧光的方法来研究 G-蛋白偶联受体 (GPCR) 与其配体之间相互作用的计划的一部分，报道了低分子量荧光标记神经肽 Y (NPY) Y5 拮抗剂的制备。强效喹唑啉型 NPY Y5 受体拮抗剂 CGP 71683A 中的萘磺酰基被丹磺酰基、硝基苯并恶二唑 (NBD) 或吖啶 - 9 - 羰基取代。在对表达人类 Y5 受体的 HEC-1B 细胞的放射性配体结合研究中，用吖啶 (Ki 311 nM) 和 NBD (Ki> 1000 nM) 标记的物质分别被证明具有中等活性或无活性。相比之下，丹酰类似物的 Ki 值为 49 nM，而 CGP 71683A 的 Ki 值为 2 nM。不与 Y1 受体结合（SK-N-MC 细胞，
• Design, synthesis and SAR of a series of 2-substituted 4-amino-quinazoline neuropeptide Y Y 5 receptor antagonists
  作者：Heinrich Rueeger、Pascal Rigollier、Yasuchika Yamaguchi、Tibur Schmidlin、Walter Schilling、Leoluca Criscione、Steven Whitebread、Michele Chiesi、Mary W Walker、Dale Dhanoa、Imadul Islam、Jack Zhang、Charles Gluchowski

  DOI：10.1016/s0960-894x(00)00177-3

  日期：2000.6

  The design of a novel series of NPY-Y-5 receptor antagonists is described. Key elements for the design were the identification of weak Y-5 hits from a Y-1 program, results from a combinatorial approach and database mining. This led to the discovery of the quinazoline 4 and the aryl-sulphonamide moiety as major components of the pharmacophore for Y-5 affinity. The synthesis and SAR towards CGP71683A is described. (C) 2000 Elsevier Science Ltd. All rights reserved.