5-chloro-2-hydroxy-N-(4-phenoxyphenyl)benzamide | 35734-66-8

• 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-(4-phenoxyphenyl)benzamide
• 英文别名: 5-Chlor-4'-phenoxy-salicylanilid
• CAS: 35734-66-8
• 化学式: C₁₉H₁₄ClNO₃
• 分子量: 339.778
• InChiKey: BPDUWOJWJYRFHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-氯代水杨酸 、 4-氨基二苯醚 在 吡啶 、 三氯化磷 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以16%的产率得到5-chloro-2-hydroxy-N-(4-phenoxyphenyl)benzamide
  参考文献：
  名称：

  Structure–activity relationships of antitubercular salicylanilides consistent with disruption of the proton gradient via proton shuttling

  摘要：

  A series of salicylanilides was synthesized based on a high-throughput screening hit against Mycobacterium tuberculosis. A free phenolic hydroxyl on the salicylic acid moeity is required for activity, and the structure-activity relationship of the aniline ring is largely driven by the presence of electron withdrawing groups. We synthesized 94 analogs exploring substitutions of both rings and the linker region in this series and we have identified multiple compounds with low micromolar potency. Unfortunately, cytotoxicity in a murine macrophage cell line trends with antimicrobial activity, suggesting a similar mechanism of action. We propose that salicylanilides function as proton shuttles that kill cells by destroying the cellular proton gradient, limiting their utility as potential therapeutics. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2012.10.056

文献信息

• [EN] COMPOUNDS AND METHODS OF INHIBITING BACTERIAL CHAPERONIN SYSTEMS<br/>[FR] COMPOSÉS ET PROCÉDÉS D'INHIBITION DE SYSTÈMES DE CHAPERONINES BACTÉRIENNES
  申请人：UNIV INDIANA TRUSTEES

  公开号：WO2022103572A1

  公开（公告）日：2022-05-19

  The present disclosure relates to compounds and methods of killing or inhibiting the growth of bacteria by disrupting chaperonin-mediated refolding of proteins.

  本公开涉及通过干扰分子伴侣介导的蛋白质重折叠来杀死或抑制细菌生长的化合物和方法。
• Structure–activity relationships of antitubercular salicylanilides consistent with disruption of the proton gradient via proton shuttling
  作者：Ill-Young Lee、Todd D. Gruber、Amanda Samuels、Minhan Yun、Bora Nam、Minseo Kang、Kathryn Crowley、Benjamin Winterroth、Helena I. Boshoff、Clifton E. Barry

  DOI：10.1016/j.bmc.2012.10.056

  日期：2013.1

  A series of salicylanilides was synthesized based on a high-throughput screening hit against Mycobacterium tuberculosis. A free phenolic hydroxyl on the salicylic acid moeity is required for activity, and the structure-activity relationship of the aniline ring is largely driven by the presence of electron withdrawing groups. We synthesized 94 analogs exploring substitutions of both rings and the linker region in this series and we have identified multiple compounds with low micromolar potency. Unfortunately, cytotoxicity in a murine macrophage cell line trends with antimicrobial activity, suggesting a similar mechanism of action. We propose that salicylanilides function as proton shuttles that kill cells by destroying the cellular proton gradient, limiting their utility as potential therapeutics. Published by Elsevier Ltd.