5-chloro-2-hydroxy-N-(3,4,5-trimethoxy)phenylbenzamide | 1043302-43-7

• 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-(3,4,5-trimethoxy)phenylbenzamide
• 英文别名: 5-chloro-2-hydroxy-N-(3,4,5-trimethoxyphenyl)benzamide
• CAS: 1043302-43-7
• 化学式: C₁₆H₁₆ClNO₅
• 分子量: 337.76
• InChiKey: TYYITJJCFISFJT-UHFFFAOYSA-N

物化性质

• 沸点：
  417.7±45.0 °C(Predicted)
• 密度：
  1.347±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  77
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-chloro-2-hydroxy-N-(3,4,5-trimethoxy)phenylbenzamide 、 2,3-bis(bromomethyl)pyrido[2,3-g]quinoxaline 在 苄基三甲基氯化铵 、 sodium hydroxide 作用下， 以 氯仿 、 水 为溶剂， 以90 %的产率得到
  参考文献：
  名称：

  发现基于吡啶喹啉的新型 P-gp 抑制剂作为癌症多重耐药性的辅助作用

  摘要：

  多重耐药性 （MDR） 是当代临床实践中一个严峻的挑战，是导致癌症药物治疗失败的主要原因。一些实验证据将 MDR 与药物外排转运蛋白 P-gp 的过表达联系起来，因此，需要发现新型 P-糖蛋白抑制剂来治疗或预防 MDR，并改善化疗药物通过胃肠道系统的吸收。在这项工作中，我们探索了一系列由亲本化合物设计的新型基于吡啶喹喔啉的衍生物，这些衍生物先前已被证明在增强 MDR 鼻咽癌 （KB） 的抗癌药物方面具有活性。其中，与参考化合物 （MK-571、Novobiocin、Verapamil） 相比，衍生物 10d 显示出对荧光染料外流的最有效和选择性抑制，并且在与化疗药物长春新碱和依托泊苷以非细胞毒性浓度共同给药时具有最高的 MDR 逆转活性。分子建模预测了两种化合物与目标蛋白的 2：1 结合模式。在健康的小胶质细胞中未观察到细胞毒性，脱靶调查显示不存在 CaV1.2 通道阻断。综上所述，我们的研究结果表明，10d

  DOI：

  10.1016/j.ejmech.2024.116647
• 作为产物：
  描述：

  5-氯代水杨酸 、 3,4,5-三甲氧基苯胺 在 三氯化磷 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 1.5h， 生成 5-chloro-2-hydroxy-N-(3,4,5-trimethoxy)phenylbenzamide
  参考文献：
  名称：

  Salicylanilide Inhibitors of Toxoplasma gondii

  摘要：

  Toxoplasma gondii (T. gondii) is an apicomplexan parasite that can cause eye disease, brain disease, and death, especially in congenitally infected and immune-compromised people. Novel medicines effective against both active and latent forms of the parasite are greatly needed. The current study focused on the discovery of such medicines by exploring a family of potential inhibitors whose antiapicomplexan activity has not been previously reported. Initial screening efforts revealed that niclosamide, a drug approved for anthelmintic use, possessed promising activity in vitro against T. gondii. This observation inspired the evaluation of the activity of a series of salicylanilides and derivatives. Several inhibitors with activities in the nanomolar range with no appreciable in vitro toxicity to human cells were identified. An initial structure activity relationship was explored. Four compounds were selected for evaluation in an in vivo model of infection, and two derivatives with potentially enhanced pharmacological parameters demonstrated the best activity profiles.

  DOI：

  10.1021/jm3007596

文献信息

• COMPOUNDS, COMPOSITIONS, AND METHODS FOR USE IN TREATING AUTOPHAGY-ASSOCIATED DISORDERS
  申请人：Biophagy, Inc.

  公开号：US20200190007A1

  公开（公告）日：2020-06-18

  The invention provides compounds and methods of treating autophagy mediated diseases and disorders and related pharmaceutical compositions, diagnostics, screening techniques and kits.

  本发明提供了化合物及其治疗自噬介导的疾病和障碍的方法，以及相关的药物组合物、诊断、筛选技术和试剂盒。
• Compounds, compositions, and methods for use in treating autophagy-associated disorders
  申请人：Biophagy, Inc.

  公开号：US11208371B2

  公开（公告）日：2021-12-28

  The invention provides compounds and methods of treating autophagy mediated diseases and disorders and related pharmaceutical compositions, diagnostics, screening techniques and kits.

  本发明提供了治疗自噬介导的疾病和失调的化合物和方法，以及相关的药物组合物、诊断方法、筛选技术和试剂盒。
• [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.
• [EN] COMPOUNDS, COMPOSITIONS, AND METHODS FOR USE IN TREATING AUTOPHAGY-ASSOCIATED DISORDERS<br/>[FR] COMPOSÉS, COMPOSITIONS ET PROCÉDÉS DESTINÉS À ÊTRE UTILISÉS DANS LE TRAITEMENT DE TROUBLES ASSOCIÉS À L'AUTOPHAGIE
  申请人：BIOPHAGY INC

  公开号：WO2020131924A1

  公开（公告）日：2020-06-25

  The invention provides compounds and methods of treating autophagy mediated diseases and disorders and related pharmaceutical compositions, diagnostics, screening techniques and kits.