trans-4-[(2-fluorobenzenesulfonamido)methyl]cyclohexanecarboxylic acid | 324756-11-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: trans-4-[(2-fluorobenzenesulfonamido)methyl]cyclohexanecarboxylic acid
• CAS: 324756-11-8
• 化学式: C₁₄H₁₈FNO₄S
• 分子量: 315.366
• InChiKey: XUVTXMUAMNJAFL-XYPYZODXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  trans-4-[(2-fluorobenzenesulfonamido)methyl]cyclohexanecarboxylic acid 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-[(2-Fluoro-benzenesulfonylamino)-methyl]-cyclohexanecarboxylic acid (6-fluoro-1-pyridin-3-ylmethyl-1,2,3,4-tetrahydro-naphthalen-2-yl)-amide
  参考文献：
  名称：

  α-Substituted N-(Sulfonamido)alkyl-β-aminotetralins:  Potent and Selective Neuropeptide Y Y5 Receptor Antagonists

  摘要：

  DOI：

  10.1021/jm990468g
• 作为产物：
  描述：

  2-氟苯磺酰氯 、 tranexamic acid 在 sodium hydroxide 作用下， 以 氯仿 为溶剂， 反应 48.0h， 生成 trans-4-[(2-fluorobenzenesulfonamido)methyl]cyclohexanecarboxylic acid
  参考文献：
  名称：

  Synthesis and evaluation of new arylsulfonamidomethylcyclohexyl derivatives as human neuropeptide Y Y5 receptor antagonists for the treatment of obesity

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2003.10.001

文献信息

• Amine and amide derivatives as ligands for the neuropeptide Y Y5 receptor useful in the treatment of obesity and other disorders
  申请人：——

  公开号：US20020115715A1

  公开（公告）日：2002-08-22

  Amine and amide derivatives of the formula: 1 which are ligands for the neuropeptide Y Y5 (NPY5) receptor, methods of preparation and pharmaceutical compositions containing amines and amides of formula A as the active ingredient are described. The amines and amides of formula A are useful in the treatment of disorders and diseases associated with NPY receptor subtype Y5.

  本文描述了公式1的胺和酰胺衍生物，它们是神经肽Y Y5（NPY5）受体的配体，还描述了制备方法和包含公式A的胺和酰胺作为活性成分的制药组合物。公式A的胺和酰胺在治疗与NPY受体亚型Y5相关的疾病和疾病方面是有用的。
• 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.
• N -(Sulfonamido)alkyl[tetrahydro-1 H -benzo[ e ]indol-2-yl]amines: potent antagonists of human neuropeptide Y Y5 receptor
  作者：James J. McNally、Mark A. Youngman、Timothy W. Lovenberg、Diane H. Nepomuceno、Sandy J. Wilson、Scott L. Dax

  DOI：10.1016/s0960-894x(99)00676-9

  日期：2000.2

  [3a,4,5,9b-Tetrahydro-1H-benzo[e]indol-2-yl]amines were prepared via reductive amination and concomitant cyclization of alpha-cyanomethyl-beta-aminotetralins. N-acylation with Omega-sulfonamido-carboxylic acids and subsequent reduction afforded a series of N-(sulfonamido)alkyl[tetrahydro-1H-benzo[e]indol-2-yl]amines, which bound to the human neuropeptide Y Y5 receptor with nanomolar affinity. (C) 2000 Elsevier Science Ltd. All rights reserved.
• AMINE AND AMIDE DERIVATIVES AS LIGANDS FOR THE NEUROPEPTIDE Y Y5 RECEPTOR USEFUL IN THE TREATMENT OF OBESITY AND OTHER DISORDERS
  申请人：Ortho-McNeil Pharmaceutical, Inc.

  公开号：EP1202986A1

  公开（公告）日：2002-05-08
• US6380224B1
  申请人：——

  公开号：US6380224B1

  公开（公告）日：2002-04-30