4-(4-cyano-naphthalene-1-sulfonylamino)-piperidine-1-carboxylic acid ethyl ester | 928236-87-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(4-cyano-naphthalene-1-sulfonylamino)-piperidine-1-carboxylic acid ethyl ester
• 英文别名: ethyl 4-((4-cyanonaphthalene)-1-sulfonamido)piperidine-1-carboxylate；Ethyl 4-[(4-cyanonaphthalen-1-yl)sulfonylamino]piperidine-1-carboxylate
• CAS: 928236-87-7
• 化学式: C₁₉H₂₁N₃O₄S
• 分子量: 387.459
• InChiKey: FMFFADYZCVXEDJ-UHFFFAOYSA-N

物化性质

• 沸点：
  593.9±60.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(4-cyano-naphthalene-1-sulfonylamino)-piperidine-1-carboxylic acid ethyl ester 在 sodium tetrahydroborate 、 cobalt(II) chloride 作用下， 以 乙醇 为溶剂， 反应 1.08h， 以43%的产率得到4-(4-aminomethyl-naphthalene-1-sulfonylamino)-piperidine-1-carboxylic acid ethyl ester
  参考文献：
  名称：

  [EN] CCR8 INHIBITORS
  [FR] INHIBITEURS DU CCR8

  摘要：

  揭示了由结构式（I）代表的CCR8抑制剂。结构式（I）中的变量在此处描述。还揭示了通过向受试者施用所披露的CCR8抑制剂之一来治疗CCR8介导的疾病，特别是哮喘的方法。

  公开号：

  WO2004058709A1
• 作为产物：
  描述：

  4-(4-fluoro-naphthalene-1-sulfonylamino)-piperidine-1-carboxylic acid ethyl ester 、 氰化钠 在 四丁基溴化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 以82%的产率得到4-(4-cyano-naphthalene-1-sulfonylamino)-piperidine-1-carboxylic acid ethyl ester
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Naphthalene-Sulfonamide Antagonists of Human CCR8

  摘要：

  The design, synthesis, and structure-activity relationship development of naphthalene-derived human CCR8 antagonists is described. In vitro binding assay results of these investigations are reported, critical interactions of the antagonists with CCR8 are defined, and preliminary physicochemical and pharmacokinetic data for the naphthalene scaffold are presented.

  DOI：

  10.1021/jm061118e

文献信息

• [EN] CCR8 INHIBITORS<br/>[FR] INHIBITEURS DE CCR8
  申请人：MILLENNIUM PHARM INC

  公开号：WO2004058736A1

  公开（公告）日：2004-07-15

  Disclosed is an inhibitor of CCR8 that is represented by Structural Formula (I). Also disclosed are pharmaceutical compositions comprising a pharmaceutically acceptable carrier or diluent and a CCR8 inhibitor represented by Structural Formula (I). Also disclosed is a method of treating inflammatory disorders in a subject by administering a CCR8 inhibitor to the subject.

  揭示了一种由结构式（I）表示的CCR8抑制剂。还揭示了包括药用载体或稀释剂和由结构式（I）表示的CCR8抑制剂的药物组合物。还揭示了通过向受试者施用CCR8抑制剂来治疗炎症性疾病的方法。
• Aryl sulfonamides useful as inhibitors of chemokine receptor activity
  申请人：Dai Mingshi

  公开号：US20050085518A1

  公开（公告）日：2005-04-21

  The present invention provides compounds of general formula I: or a pharmaceutically acceptable salt thereof, wherein R 1 , X, Z, R 2 , X., Ar, n, R 3 and R 4 are defined generally and in subsets herein. Compounds of the invention are inhibitors of CCR8 and accordingly are useful for the treatment of a variety of inflammatory and allergic disorders.

  本发明提供一般式I的化合物:或其药学上可接受的盐，其中R1、X、Z、R2、X.、Ar、n、R3和R4在本文中一般和子集中定义。本发明的化合物是CCR8的抑制剂，因此可用于治疗各种炎症和过敏性疾病。
• CCR8 Inhibitors
  申请人：Millennium Pharmaceuticals, Inc.

  公开号：US20040209948A1

  公开（公告）日：2004-10-21

  Disclosed are CCR8 inhibitors represented by Structural Formulas (I): 1 The variables in Structural Formula (I) are described herein. Also disclosed are methods of treating a subject with a CCR8 mediated condition, especially asthma, by administering one of the disclosed CCR8 inhibitors to the subject.

  本发明涉及由结构式（I）表示的CCR8抑制剂：1结构式（I）中的变量在此文中进行了描述。本发明还涉及通过向受试者给予所披露的CCR8抑制剂之一来治疗CCR8介导的疾病，特别是哮喘的方法。
• CCR8 inhibitors
  申请人：Millennium Pharmaceuticals, Inc.

  公开号：US20040224978A1

  公开（公告）日：2004-11-11

  Disclosed is an inhibitor of CCR8 that is represented by Structural Formula (I): 1 Also disclosed are pharmaceutical compositions comprising a pharmaceutically acceptable carrier or diluent and a CCR8 inhibitor represented by Structural Formula (I). Also disclosed is a method of treating inflammatory disorders in a subject by administering a CCR8 inhibitor to the subject.

  本发明揭示了一种由结构式(I)所代表的CCR8抑制剂：1。还揭示了包含药学上可接受的载体或稀释剂以及由结构式(I)所代表的CCR8抑制剂的药物组合物。同时还揭示了通过向受试者施用CCR8抑制剂来治疗炎症性疾病的方法。
• Identification of novel human CC chemokine receptor 8 (CCR8) antagonists via the synthesis of naphthalene amide and sulfonamide isosteres
  作者：Yenthel Verhaegen、Libao Liu、Tien T. Nguyen、Tom Van Loy、Dominique Schols、Arnout R.D. Voet、Wim Dehaen、Steven De Jonghe

  DOI：10.1016/j.bioorg.2024.107181

  日期：2024.4

  The human CC chemokine receptor 8 (CCR8) has been extensively pursued as target for the treatment of various inflammatory disorders. More recently, the importance of CCR8 in the tumor microenvironment has been demonstrated, spurring the interest in CCR8 antagonism as therapeutic strategy in immuno-oncology. On a previously described naphthalene sulfonamide with CCR8 antagonistic properties, the concept

  人类 CC 趋化因子受体 8 (CCR8) 已被广泛用作治疗各种炎症性疾病的靶点。最近，CCR8 在肿瘤微环境中的重要性已被证明，激发了人们对 CCR8 拮抗作为免疫肿瘤学治疗策略的兴趣。在先前描述的具有 CCR8 拮抗特性的萘磺酰胺上，应用电子等排的概念，导致在 CCL1 竞争结合和 CCR8 钙动员测定中发现了 IC 值在 nM 范围内的新型 CCR8 拮抗剂。通过同源分子模型合理化了最有效的同系物的优异 CCR8 拮抗活性。