5-chloro-2-hydroxy- N-[(2S)-3-methyl-1-oxo-1-{[4-(trifluoromethyl)phenyl]amino}butan-2-yl]benzamide | 1227477-16-8

• 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-[(2S)-3-methyl-1-oxo-1-{[4-(trifluoromethyl)phenyl]amino}butan-2-yl]benzamide
• 英文别名: 5-chloro-2-hydroxy-N-[(1S)-2-methyl-1-[[4-(trifluoromethyl)phenyl]carbamoyl]propyl]benzamide；5-chloro-2-hydroxy-N-[(2S)-3-methyl-1-oxo-1-[4-(trifluoromethyl)anilino]butan-2-yl]benzamide
• CAS: 1227477-16-8
• 化学式: C₁₉H₁₈ClF₃N₂O₃
• 分子量: 414.812
• InChiKey: SMJZGDRVSORQDF-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-chloro-N-(4-(trifluoromethyl)phenyl)-2-hydroxybenzamide 在 氢溴酸 、 溶剂黄146 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 5-chloro-2-hydroxy- N-[(2S)-3-methyl-1-oxo-1-{[4-(trifluoromethyl)phenyl]amino}butan-2-yl]benzamide
  参考文献：
  名称：

  New derivatives of salicylamides: Preparation and antimicrobial activity against various bacterial species

  摘要：

  Three series of salicylanilides, esters of N-phenylsalicylamides and 2-hydroxy-N-[1-(2-hydroxyphenylamino)-1-oxoalkan-2-yl]benzamides, in total thirty target compounds were synthesized and characterized. The compounds were evaluated against seven bacterial and three mycobacterial strains. The antimicrobial activities of some compounds were comparable or higher than the standards ampicillin, ciprofloxacin or isoniazid. Derivatives 3f demonstrated high biological activity against Staphylococcus aureus (<= 0.03 mu mol/L), Mycobacterium marinum (<= 0.40 mu mol/L) and Mycobacterium kansasii (1.58 mu mol/L), 3g shows activity against Clostridium perfringens (<= 0.03 mu mol/L) and Bacillus cereus (0.09 mu mol/L), 3h against Pasteurella multocida (<= 0.03 mu mol/L) and M. kansasii (<= 0.43 mu mol/L), 3i against methicillin-resistant S. aureus and B. cereus (<= 0.03 mu mol/L). The structure-activity relationships are discussed for all the compounds. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.08.029

文献信息

• In vitro activity of salicylamide derivatives against vancomycin-resistant enterococci
  作者：Sarka Pospisilova、Hana Michnova、Tereza Kauerova、Karel Pauk、Peter Kollar、Jarmila Vinsova、Ales Imramovsky、Alois Cizek、Josef Jampilek

  DOI：10.1016/j.bmcl.2018.05.011

  日期：2018.7

  A series of 13 salicylamide derivatives was assessed for antibacterial activity against three isolates of vancomycin-resistant Enterococcus faecalis (VRE) and Enterococcus faecalis ATCC 29212 as a quality standard. The minimum inhibitory concentration was determined by the broth microdilution method with subsequent subcultivation of aliquots to assess minimum bactericidal concentration. The growth

  评估了一系列13种水杨酰胺衍生物对耐万古霉素的粪肠球菌（VRE）和粪肠球菌的三种分离物的抗菌活性ATCC 29212作为质量标准。通过肉汤微量稀释法确定最小抑制浓度，随后将等分试样亚培养，以评估最小杀菌浓度。通过时间杀灭试验确定生长动力学。氨苄西林，环丙沙星，四环素和万古霉素被用作参考抗菌药物。被研究的化合物中的三个对VRE（0.199–25 µM）表现出强大的抑菌活性，与氨苄西林和环丙沙星相比具有更强的抑菌活性。此外，还测试了这些化合物与万古霉素，环丙沙星和四环素的协同作用，而5-氯-2-羟基-N-[4-（三氟甲基）苯基]苯甲酰胺显示出最高的效力，并且与万古霉素对VRE 368有协同活性。使用人单核细胞白血病THP-1细胞并根据LD 50筛选最有效的化合物的细胞毒性值，可以说该化合物对人细胞的毒性微不足道。
• Synthetic Route for the Preparation of 2-Hydroxy-<i>N</i>-[1-(2-hydroxyphenylamino)-1-oxoalkan-2-yl]benzamides
  作者：Aleš Imramovský、Juana M. Férriz、Karel Pauk、Martin Krátký、Jarmila Vinšová

  DOI：10.1021/cc900168s

  日期：2010.7.12