Benzoic acid, 5-chloro-2-hydroxy-, 3,5-bis(trifluoromethyl)phenyl ester | 634184-76-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: Benzoic acid, 5-chloro-2-hydroxy-, 3,5-bis(trifluoromethyl)phenyl ester
• 英文别名: [3,5-bis(trifluoromethyl)phenyl] 5-chloro-2-hydroxybenzoate
• CAS: 634184-76-2
• 化学式: C₁₅H₇ClF₆O₃
• 分子量: 384.662
• InChiKey: VTOCOJLNMRXIBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  5-氯代水杨酸 、 3,5-二三氟甲基苯酚 在 三氯氧磷 作用下， 以 xylene 为溶剂， 反应 2.0h， 以13.9%的产率得到Benzoic acid, 5-chloro-2-hydroxy-, 3,5-bis(trifluoromethyl)phenyl ester
  参考文献：
  名称：

  EP1510207

  摘要：

  公开号：

文献信息

• EP1510210
  申请人：——

  公开号：——

  公开（公告）日：——
• EP1512396
  申请人：——

  公开号：——

  公开（公告）日：——
• EP1514544
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.