5-chloro-2-hydroxy-N-(3-methyl-4-nitrophenyl)benzamide | 1187819-34-6

• 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: 5-chloro-2-hydroxy-N-(3-methyl-4-nitrophenyl)benzamide
• CAS: 1187819-34-6
• 化学式: C₁₄H₁₁ClN₂O₄
• 分子量: 306.705
• InChiKey: YOKSMYCXNBMQEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  95.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-氯代水杨酸 在 4-二甲氨基吡啶 、 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 为溶剂， 生成 5-chloro-2-hydroxy-N-(3-methyl-4-nitrophenyl)benzamide
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Niclosamide Analogs as Therapeutic Agents for Enzalutamide-Resistant Prostate Cancer

  摘要：

  尼可刹米能有效下调雄激素受体变体（AR-Vs），用于治疗恩杂鲁胺和阿比特龙耐药的前列腺癌。然而，由于尼可刹米的溶解性和代谢不稳定性，其药物特性较差，限制了其作为全身性癌症治疗药物的临床应用。本研究制备了一系列新型尼可刹米类似物，以系统地探索其结构-活性关系，并在尼可刹米骨架化学结构的基础上鉴定出具有更好药物特性的活性 AR-Vs 抑制剂。利用 1H NMR、13C NMR、MS 和元素分析对化合物进行了表征。对合成的化合物进行了评估，以确定其在两种耐恩扎鲁胺细胞系（LNCaP95 和 22RV1）中的抗增殖活性以及对 AR 和 AR-V7 的下调作用。几种烟酰胺类似物在 LNCaP95 和 22RV1 细胞系中表现出了同等或更好的抗增殖效果（B9，IC50 LNCaP95 和 22RV1 分别为 0.130 和 0.0997 μM）、强效的 AR-V7 下调活性以及更好的代谢稳定性。此外，还进行了传统的结构-活性关系（SAR）和三维-QSAR 分析，以指导进一步的结构优化。活性最高的 B9 的两个 -CF3 基团位于立体有利区域，而活性最低的 B7 的 -CN 基团位于立体不利区域，这似乎使 B9 的抗增殖活性比 B7 更强。

  DOI：

  10.3390/ph16050735

文献信息

• Glutamate receptor modulators and therapeutic agents
  申请人：Wood Richard Delarey

  公开号：US20090239919A1

  公开（公告）日：2009-09-24

  The present invention discloses methods of modulating the activity of Group I mGluRs using a defined class of benzamide compounds. In one embodiment, methods of modulating the activity of mGluR1 are provided. In another embodiment, methods of modulating the activity of mGluR5 are provided. In still another embodiment, methods of simultaneously modulating the activities of both mGluR1 and mGluR5 are provided. The present invention also provides methods of treating diseases or disorders which are mediated in full or in part by Group I mGluRs using one or more compounds belonging to the defined class of benzamide compounds. The present invention further provides methods of preventing diseases or disorders which are mediated in full or in part by Group I mGluRs using one or more compounds belonging to the defined class of compounds. Diseases and disorders contemplated include, inter alia, diseases and disorders of the central nervous system, the peripheral nervous system, the gastrointestinal system, the circulatory system, skin, retina, brain, heart, and lungs.

  本发明公开了利用一类明确定义的苯甲酰胺化合物调节I类mGluRs活性的方法。在一个实施例中，提供了调节mGluR1活性的方法。在另一个实施例中，提供了调节mGluR5活性的方法。在另一个实施例中，提供了同时调节mGluR1和mGluR5活性的方法。本发明还提供了利用属于明确定定义的苯甲酰胺化合物类的一个或多个化合物治疗由I类mGluRs完全或部分介导的疾病或紊乱的方法。本发明还提供了利用属于明确定定义的化合物类的一个或多个化合物预防由I类mGluRs完全或部分介导的疾病或紊乱的方法。所考虑的疾病和紊乱包括中枢神经系统、外周神经系统、胃肠系统、循环系统、皮肤、视网膜、大脑、心脏和肺等疾病和紊乱。
• [EN] GLUTAMATE RECEPTOR MODULATORS AND THERAPEUTIC AGENTS<br/>[FR] MODULATEURS DES RÉCEPTEURS AU GLUTAMATE ET AGENTS THÉRAPEUTIQUES
  申请人：WOOD RICHARD D

  公开号：WO2010101648A1

  公开（公告）日：2010-09-10

  The present invention discloses methods of modulating the activity of Group I mGluRs using a defined class of benzamide compounds. In one embodiment, methods of modulating the activity of mGluR1 are provided. In another embodiment, methods of modulating the activity of mGluR5 are provided. In still another embodiment, methods of simultaneously modulating the activities of both mGluR1 and mGluR5 are provided. The present invention also provides methods of treating diseases or disorders which are mediated in full or in part by Group I mGluRs using one or more compounds belonging to the defined class of benzamide compounds. The present invention further provides methods of preventing diseases or disorders which are mediated in full or in part by Group I mGluRs using one or more compounds belonging to the defined class of compounds. Diseases and disorders contemplated include, inter alia, diseases and disorders of the central nervous system, the peripheral nervous system, the gastrointestinal system, the circulatory system, skin, retina, brain, heart, and lungs.