(1r,4r)-N1,N4-diphenylcyclohexane-1,4-dicarboxamide | 898191-56-5

• 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: (1r,4r)-N1,N4-diphenylcyclohexane-1,4-dicarboxamide
• CAS: 898191-56-5
• 化学式: C₂₀H₂₂N₂O₂
• 分子量: 322.407
• InChiKey: WPMXHFCEZBAZLM-WKILWMFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  58.2
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1r,4r)-N1,N4-diphenylcyclohexane-1,4-dicarboxamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以255.3 mg的产率得到MSX-171
  参考文献：
  名称：

  Discovery of Small Molecule CXCR4 Antagonists

  摘要：

  In light of a proposed molecular mechanism for the C-X-C chemokine receptor type 4 (CXCR4) antagonist 1 (AMD3100), a template with the general structure 2 was designed, and 15 was identified as a lead by means of an affinity binding assay against the ligand-mimicking CXCR4 antagonist 3 (TN14003). Following a structure-activity profile around 15, the design and synthesis of a series of novel small molecular CXCR4 antagonists led to the discovery of 32 (WZ811). The compound shows subnanomolar potency (EC50 = 0.3 nM) in an affinity binding assay. In addition, when subjected to in vitro functional evaluation, 32 efficiently inhibits CXCR4/stromal cell-derived factor-1 (SDF-1)-mediated modulation of cyclic adenosine monophophate (CAMP) levels (EC50 = 1.2 nM) and SDF-1 induced Matrigel invasion (EC50 = 5.2 nM). Molecular field topology analysis (MFTA), a 2D quantitative structure-activity relationship (QSAR) approach based on local molecular properties (Van der Waals radii (VdW), atomic charges, and local lipophilicity), applied to the 32 series suggests structural modifications to improve potency.

  DOI：

  10.1021/jm070679i
• 作为产物：
  描述：

  trans-1,4-Cyclohexanedicarbonyl dichloride 、 苯胺 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (1r,4r)-N1,N4-diphenylcyclohexane-1,4-dicarboxamide
  参考文献：
  名称：

  Discovery of Small Molecule CXCR4 Antagonists

  摘要：

  In light of a proposed molecular mechanism for the C-X-C chemokine receptor type 4 (CXCR4) antagonist 1 (AMD3100), a template with the general structure 2 was designed, and 15 was identified as a lead by means of an affinity binding assay against the ligand-mimicking CXCR4 antagonist 3 (TN14003). Following a structure-activity profile around 15, the design and synthesis of a series of novel small molecular CXCR4 antagonists led to the discovery of 32 (WZ811). The compound shows subnanomolar potency (EC50 = 0.3 nM) in an affinity binding assay. In addition, when subjected to in vitro functional evaluation, 32 efficiently inhibits CXCR4/stromal cell-derived factor-1 (SDF-1)-mediated modulation of cyclic adenosine monophophate (CAMP) levels (EC50 = 1.2 nM) and SDF-1 induced Matrigel invasion (EC50 = 5.2 nM). Molecular field topology analysis (MFTA), a 2D quantitative structure-activity relationship (QSAR) approach based on local molecular properties (Van der Waals radii (VdW), atomic charges, and local lipophilicity), applied to the 32 series suggests structural modifications to improve potency.

  DOI：

  10.1021/jm070679i

文献信息

• Tricyclic amino containing compounds for treatment or prevention of symptoms associated with endocrine dysfunction
  申请人：Emory University

  公开号：US10632120B2

  公开（公告）日：2020-04-28

  The disclosure provides methods of use of certain compounds that are useful for treating certain symptoms of endocrine disturbances, and in particular those associated with hot flashes.

  本公开提供了某些化合物的使用方法，这些化合物可用于治疗内分泌紊乱的某些症状，尤其是与潮热相关的症状。
• Synthesis of Cycloaliphatic Polyamides via Palladium-Catalyzed Hydroaminocarbonylative Polymerization
  作者：Yaodu Zhang、Fei Wu、Hui-Yi Yang、Gang Wang、Zhi-Hui Ren、Zheng-Hui Guan

  DOI：10.1021/jacs.4c01210

  日期：2024.5.15

  materials, proceeds in an atom-economic manner, and creates a series of new functional polyamides in high yields and high molecular weights. In contrast with the traditional polyamides based on adipic acid, the cycloaliphatic polyamides have superior thermal resistance, higher glass-transition temperature, and better solubility in common organic solvents, thus probably featuring the merits of high-performance

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• TRICYCLIC AMINO CONTAINING COMPOUNDS FOR TREATMENT OR PREVENTION OF SYMPTOMS ASSOCIATED WITH ENDOCRINE DYSFUNCTION
  申请人：Emory University

  公开号：EP2776387B1

  公开（公告）日：2017-02-01
• CXCR4 antagonists for the treatment of medical disorders
  申请人：Shim Hyunsuk

  公开号：US20070054930A1

  公开（公告）日：2007-03-08

  The invention provides compounds, pharmaceutical compositions and methods of use of certain compounds that are antagonists of the chemokine CXCR4 receptor for the treatment of proliferative conditions mediated by CXCR4 receptors. The compounds provided interfere with the binding of SDF1 to the receptor. These compounds are particularly useful for treating or reducing the severity of hyperproliferative diseases by inhibiting metastasis.
• CXCR4 ANTAGONISTS FOR THE TREATMENT OF MEDICAL DISORDERS
  申请人：Shim Hyunsuk

  公开号：US20140039187A1

  公开（公告）日：2014-02-06

  The invention provides compounds, pharmaceutical compositions and methods of use of certain compounds that are antagonists of the chemokine CXCR4 receptor for the treatment of proliferative conditions mediated by CXCR4 receptors. The compounds provided interfere with the binding of SDF1 to the receptor. These compounds are particularly useful for treating or reducing the severity of hyperproliferative diseases by inhibiting metastasis.