4-chloro-N-{(2S)-1-[(3,4-dichlorophenyl)amino]-3-methyl-1-oxobutan-2-yl}-2-hydroxybenzamide | 1227477-32-8

• 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: 4-chloro-N-{(2S)-1-[(3,4-dichlorophenyl)amino]-3-methyl-1-oxobutan-2-yl}-2-hydroxybenzamide
• 英文别名: 4-chloro-N-[(1S)-1-[(3,4-dichlorophenyl)carbamoyl]-2-methyl-propyl]-2-hydroxy-benzamide；4-chloro-N-[(2S)-1-(3,4-dichloroanilino)-3-methyl-1-oxobutan-2-yl]-2-hydroxybenzamide
• CAS: 1227477-32-8
• 化学式: C₁₈H₁₇Cl₃N₂O₃
• 分子量: 415.704
• InChiKey: NIGYINYFBYFWJV-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-chloro-N-(3,4-dichlorophenyl)-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 4-chloro-N-{(2S)-1-[(3,4-dichlorophenyl)amino]-3-methyl-1-oxobutan-2-yl}-2-hydroxybenzamide
  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

• 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
• New derivatives of salicylamides: Preparation and antimicrobial activity against various bacterial species
  作者：Karel Pauk、Iveta Zadražilová、Aleš Imramovský、Jarmila Vinšová、Michaela Pokorná、Martina Masaříková、Alois Čížek、Josef Jampílek

  DOI：10.1016/j.bmc.2013.08.029

  日期：2013.11

  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.