4-[(Naphthalene-1-sulfonylamino)-methyl]-cyclohexanecarboxylic acid | 192322-99-9

• 英文名称: 4-[(Naphthalene-1-sulfonylamino)-methyl]-cyclohexanecarboxylic acid
• CAS: 192322-99-9
• 化学式: C₁₈H₂₁NO₄S
• 分子量: 347.435
• InChiKey: QSKZQKQSDYMLPZ-CTYIDZIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  83.47
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-[(Naphthalene-1-sulfonylamino)-methyl]-cyclohexanecarboxylic acid 在 sodium azide 、 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 生成
  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
• 作为产物：
  描述：

  1-萘磺酰氯 、 tranexamic acid 在 sodium hydroxide 作用下， 以80%的产率得到4-[(Naphthalene-1-sulfonylamino)-methyl]-cyclohexanecarboxylic acid
  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

• Synthesis and evaluation of new hydrazide derivatives as neuropeptide Y Y5 receptor antagonists for the treatment of obesity
  作者：Laura Juanenea、Silvia Galiano、Oihana Erviti、Antonio Moreno、Silvia Pérez、Ignacio Aldana、Antonio Monge

  DOI：10.1016/j.bmc.2004.06.023

  日期：2004.9

  NPY is the most potent orexigenic agent known to man, with NPY Y1 and NPY Y5 being the receptor subtypes that are most likely responsible for centrally-mediated NPY-induced feeding responses. Based on the aforementioned, novel hydrazide derivatives were prepared for the purpose of searching new NPY Y5 receptor antagonists. Many of the compounds exhibited nanomolar binding affinity for this receptor, affording trans-N-4-[N'-(3,4-dichlorophenyl)hydrazinocarbonyl]cyclohexylmethyl}-4-fluorobenzenesulfonamide, which showed the best activity (IC50=0.43 nM). (C) 2004 Published by Elsevier Ltd.
• Synthesis and evaluation of new arylsulfonamidomethylcyclohexyl derivatives as human neuropeptide Y Y5 receptor antagonists for the treatment of obesity
  作者：Antonio Moreno、Silvia Pérez、Silvia Galiano、Laura Juanenea、Oihana Erviti、Carmen Frígola、Ignacio Aldana、Antonio Monge

  DOI：10.1016/j.ejmech.2003.10.001

  日期：2004.1

  NPY is the most potent orexigenic peptide identified up to now. Stimulation of food intake is measured by the Y-1 and Y-5 receptor subtypes. In this study, the synthesis and evaluation of new arylsulfonamidomethylcyclohexyl derivatives are described as potential selective antagonists of the human NPY Y-5 receptor. The SAR of these series was examined and the amide derivatives were the compounds that showed the best activities. trans-N-4-[(Quinolin-3-yl)aminocarbonyl]cyclohexylmethyl}-2,4-dichlorobenzenesulfonamide (42) bound to the human neuropeptide Y Y-5 receptor with a 2 nM IC50. (C) 2003 Elsevier SAS. All rights reserved.
• [EN] RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DE RECEPTEURS
  申请人：——

  公开号：WO1997020823A2

  公开（公告）日：1997-06-12

  [EN] The invention relates to a compound of formula (I) in which the variables are as defined and/or a salt or a tautomer thereof; and relates to a method of treatment of disorders or diseases associated with NPY receptor subtype Y5, to pharmaceutical compositions comprising a compound of formula (I) or a pharmaceutically acceptable salt thereof and to the manufacture of the compounds of formula (I) or a salt thereof.
  [FR] L'invention concerne un composé de la formule (I), dans laquelle les variables sont telles que définies, ainsi qu'un sel ou un tautomère de celui-ci. Elle concerne également une méthode de traitement des troubles et maladies associés au sous-type Y5 du récepteur du neuropeptide Y, des compositions pharmaceutiques comprenant un composé de la formule (I) ou un sel de celui-ci acceptable sur le plan pharmacologique, ainsi que la fabrication des composés de la formule (I) ou d'un sel de ceux-ci.