(S)-4-chloro-2-(3,4-dichlorophenylcarbamoyl)phenyl 2-acetamido-3-phenylpropanoate | 1261296-10-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-4-chloro-2-(3,4-dichlorophenylcarbamoyl)phenyl 2-acetamido-3-phenylpropanoate
• 英文别名: [4-chloro-2-[(3,4-dichlorophenyl)carbamoyl]phenyl] (2S)-2-acetamido-3-phenylpropanoate
• CAS: 1261296-10-9
• 化学式: C₂₄H₁₉Cl₃N₂O₄
• 分子量: 505.785
• InChiKey: OCKMXNCZJKEYGH-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  84.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,4,5-三氯水杨苯胺 、 N-乙酰-L-苯丙氨酸 在 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 52.0h， 以69%的产率得到(S)-4-chloro-2-(3,4-dichlorophenylcarbamoyl)phenyl 2-acetamido-3-phenylpropanoate
  参考文献：
  名称：

  New amino acid esters of salicylanilides active against MDR-TB and other microbes

  摘要：

  Eleven halogenated (S)-2-(phenylcarbamoyl)phenyl 2-acetamido-3-phenylpropanoates (3a-3k) were designed and synthesized as potential antimicrobial agents. They were evaluated in vitro against some mycobacterial, bacterial and fungal strains. These compounds were active against drug-sensitive and atypical mycobacterial strains with general MIC values from 0.25 to 16 mu mol/L. The most active compounds were (S)-4-chloro-2-(4-(trifluoromethyl)phenylcarbamoyl)phenyl 2-acetamido-3-phenylpropanoate (3i) and (S)-4-bromo-2-(4-(trifluoromethyl)phenylcarbamoyl)phenyl 2-acetamido-3-phenylpropanoate (3k) which exhibited activity against MDR and XDR-TB strains with MICs from 1 to 2 mu mol/L. 3k was shown to be less cytotoxic with higher IC50. Some compounds exhibited low MICs on Gram-positive bacteria (MICs >= 0.98 mu mol/L) and on fungi (MICs >= 3.9 mu mol/L). (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.09.040

文献信息

• New amino acid esters of salicylanilides active against MDR-TB and other microbes
  作者：Martin Krátký、Jarmila Vinšová、Vladimír Buchta、Kata Horvati、Szilvia Bösze、Jiřina Stolaříková

  DOI：10.1016/j.ejmech.2010.09.040

  日期：2010.12

  Eleven halogenated (S)-2-(phenylcarbamoyl)phenyl 2-acetamido-3-phenylpropanoates (3a-3k) were designed and synthesized as potential antimicrobial agents. They were evaluated in vitro against some mycobacterial, bacterial and fungal strains. These compounds were active against drug-sensitive and atypical mycobacterial strains with general MIC values from 0.25 to 16 mu mol/L. The most active compounds were (S)-4-chloro-2-(4-(trifluoromethyl)phenylcarbamoyl)phenyl 2-acetamido-3-phenylpropanoate (3i) and (S)-4-bromo-2-(4-(trifluoromethyl)phenylcarbamoyl)phenyl 2-acetamido-3-phenylpropanoate (3k) which exhibited activity against MDR and XDR-TB strains with MICs from 1 to 2 mu mol/L. 3k was shown to be less cytotoxic with higher IC50. Some compounds exhibited low MICs on Gram-positive bacteria (MICs >= 0.98 mu mol/L) and on fungi (MICs >= 3.9 mu mol/L). (C) 2010 Elsevier Masson SAS. All rights reserved.