(R)-2-((3,4-dichlorophenoxy)methyl)oxirane | 97097-26-2

• 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: (R)-2-((3,4-dichlorophenoxy)methyl)oxirane
• 英文别名: (2R)-2-[(3,4-dichlorophenoxy)methyl]oxirane
• CAS: 97097-26-2
• 化学式: C₉H₈Cl₂O₂
• 分子量: 219.067
• InChiKey: NRLJEEOYPXGFOM-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-[4-氯-3-(三氟甲基)苯基]-4-哌啶醇 、 (R)-2-((3,4-dichlorophenoxy)methyl)oxirane 以 乙醇 为溶剂， 以0.41 g的产率得到1-((S)-3-(3,4-dichlorophenoxy)-2-hydroxypropyl)-4-(4-chloro-3-(trifluoromethyl)phenyl)piperidin-4-ol
  参考文献：
  名称：

  Discovery, synthesis, and biological evaluation of piperidinol analogs with anti-tuberculosis activity

  摘要：

  Direct anti-tuberculosis screening of commercially available compound libraries identified a novel piperidinol with interesting anti-tuberculosis activity and drug like characteristics. To generate a structure activity relationship about this hit a 22 member optimization library was generated using parallel synthesis. Products of this library 1-((R)-3-(4-chlorophenoxy)-2-hydroxypropyl)-4-(4-chloro-3-(trifluoromethyl) phenyl) piperidin-4-ol and 1-((S)-3-(4-(trifluoromethyl) phenoxy)-2-hydroxypropyl)-4-(4-chloro-3-( trifluoromethyl) phenyl) piperidin-4-ol demonstrated good anti-tuberculosis activity. Unfortunately, side effects were observed upon in vivo anti-tuberculosis testing of these compounds precluding their further advancement, which may be in part due to the secondary pharmacology associated with the aryl piperidinol core. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.005
• 作为产物：
  描述：

  左旋环氧氯丙烷 、 3,4-二氯苯酚 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 14.0h， 以69%的产率得到(R)-2-((3,4-dichlorophenoxy)methyl)oxirane
  参考文献：
  名称：

  Modulators of cell adhesion, methods and compositions therefor

  摘要：

  揭示了作为细胞粘附调节剂的化合物。这些化合物是哌啶-4-胺的衍生物。在某些实施例中，化合物可以与靶向剂、药用活性物质和/或支持材料连接。还揭示了增强或抑制经典钙粘蛋白介导功能的方法。这些化合物可用于治疗或预防包括癌症在内的各种疾病。还揭示了包括含有化合物的皮肤贴片在内的组合物和器件。此外，还提供了化合物的合成方法。

  公开号：

  US20190100493A1

文献信息

• MODULATORS OF CELL ADHESION, METHODS AND COMPOSITIONS THEREFOR
  申请人：Blaschuk, Orest

  公开号：EP3692018A1

  公开（公告）日：2020-08-12
• [EN] MODULATORS OF CELL ADHESION, METHODS AND COMPOSITIONS THEREFOR<br/>[FR] MODULATEURS DE L'ADHÉSION CELLULAIRE, PROCÉDÉS ET COMPOSITIONS ASSOCIÉS
  申请人：BLASCHUK OREST

  公开号：WO2019070816A1

  公开（公告）日：2019-04-11

  Compounds with activity as modulators of cell adhesion are disclosed. The compounds are derivatives of piperidin-4-amine. In some embodiments, a compound can be linked to a targeting agent, a pharmaceutically active substance and/or a support material. Methods for enhancing or inhibiting classical cadherin-mediated functions are also disclosed. The compounds can be used for the treatment or prevention of a variety of diseases including cancer. Compositions and devices, including skin patches comprising a compound are also disclosed. In addition, methods of synthesis of the compounds are provided.
• Discovery, synthesis, and biological evaluation of piperidinol analogs with anti-tuberculosis activity
  作者：Dianqing Sun、Michael S. Scherman、Victoria Jones、Julian G. Hurdle、Lisa K. Woolhiser、Susan E. Knudson、Anne J. Lenaerts、Richard A. Slayden、Michael R. McNeil、Richard E. Lee

  DOI：10.1016/j.bmc.2009.04.005

  日期：2009.5

  Direct anti-tuberculosis screening of commercially available compound libraries identified a novel piperidinol with interesting anti-tuberculosis activity and drug like characteristics. To generate a structure activity relationship about this hit a 22 member optimization library was generated using parallel synthesis. Products of this library 1-((R)-3-(4-chlorophenoxy)-2-hydroxypropyl)-4-(4-chloro-3-(trifluoromethyl) phenyl) piperidin-4-ol and 1-((S)-3-(4-(trifluoromethyl) phenoxy)-2-hydroxypropyl)-4-(4-chloro-3-( trifluoromethyl) phenyl) piperidin-4-ol demonstrated good anti-tuberculosis activity. Unfortunately, side effects were observed upon in vivo anti-tuberculosis testing of these compounds precluding their further advancement, which may be in part due to the secondary pharmacology associated with the aryl piperidinol core. (C) 2009 Elsevier Ltd. All rights reserved.
• Modulators of cell adhesion, methods and compositions therefor
  申请人：Zonula Incorporated

  公开号：US20190100493A1

  公开（公告）日：2019-04-04

  Compounds with activity as modulators of cell adhesion are disclosed. The compounds are derivatives of piperidin-4-amine. In some embodiments, a compound can be linked to a targeting agent, a pharmaceutically active substance and/or a support material. Methods for enhancing or inhibiting classical cadherin-mediated functions are also disclosed. The compounds can be used for the treatment or prevention of a variety of diseases including cancer. Compositions and devices, including skin patches comprising a compound are also disclosed. In addition, methods of synthesis of the compounds are provided.

  揭示了作为细胞粘附调节剂的化合物。这些化合物是哌啶-4-胺的衍生物。在某些实施例中，化合物可以与靶向剂、药用活性物质和/或支持材料连接。还揭示了增强或抑制经典钙粘蛋白介导功能的方法。这些化合物可用于治疗或预防包括癌症在内的各种疾病。还揭示了包括含有化合物的皮肤贴片在内的组合物和器件。此外，还提供了化合物的合成方法。