(S)-N-(4-methyl-1-oxo-1-((2-propylphenyl)amino)pentan-2-yl)-4-((4-oxo-2-thioxothiazolidin-5-ylidene)methyl)benzamide | 1373268-05-3

• 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)-N-(4-methyl-1-oxo-1-((2-propylphenyl)amino)pentan-2-yl)-4-((4-oxo-2-thioxothiazolidin-5-ylidene)methyl)benzamide
• CAS: 1373268-05-3
• 化学式: C₂₆H₂₉N₃O₃S₂
• 分子量: 495.667
• InChiKey: QRRXIVHOWIVTQD-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.91
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  87.3
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  4-[(E)-(2-疏基-4-氧代-1,3-噻唑-5(4H)-基)甲基]苯甲酸 、 (2S)-2-amino-4-methyl-N-(2-propylphenyl)pentanamide 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 (S)-N-(4-methyl-1-oxo-1-((2-propylphenyl)amino)pentan-2-yl)-4-((4-oxo-2-thioxothiazolidin-5-ylidene)methyl)benzamide
  参考文献：
  名称：

  5-Benzylidenerhodanine and 5-benzylidene-2-4-thiazolidinedione based antibacterials

  摘要：

  Herein we outline the antibacterial activity of amino acid containing thiazolidinediones and rhodanines against Gram-positive bacteria Staphylococcus aureus ATCC 31890, Staphylococcus epidermidis and Bacillus subtilis ATCC 6633. The rhodanine derivatives were generally more active than the analogous thiazolidinediones. Compounds of series 5 showed some selectivity for Bacillus subtilis ATCC 6633, the extent of which is enhanced by the inclusion of a non-polar amino acid at the 5-position of the core thiazolidinediones and rhodanines scaffolds. SAR data of series 8 demonstrated improved activity against the clinically more significant Staphylococci with selectivity over Bacillus subtilis ATCC 6633 induced by introduction of a bulky aryl substituent at the 5-position of the core scaffolds. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.02.100

文献信息

• 5-Benzylidenerhodanine and 5-benzylidene-2-4-thiazolidinedione based antibacterials
  作者：Ondrej Zvarec、Steven W. Polyak、William Tieu、Kevin Kuan、Huanqin Dai、Daniel Sejer Pedersen、Renato Morona、Lixin Zhang、Grant W. Booker、Andrew D. Abell

  DOI：10.1016/j.bmcl.2012.02.100

  日期：2012.4

  Herein we outline the antibacterial activity of amino acid containing thiazolidinediones and rhodanines against Gram-positive bacteria Staphylococcus aureus ATCC 31890, Staphylococcus epidermidis and Bacillus subtilis ATCC 6633. The rhodanine derivatives were generally more active than the analogous thiazolidinediones. Compounds of series 5 showed some selectivity for Bacillus subtilis ATCC 6633, the extent of which is enhanced by the inclusion of a non-polar amino acid at the 5-position of the core thiazolidinediones and rhodanines scaffolds. SAR data of series 8 demonstrated improved activity against the clinically more significant Staphylococci with selectivity over Bacillus subtilis ATCC 6633 induced by introduction of a bulky aryl substituent at the 5-position of the core scaffolds. (C) 2012 Elsevier Ltd. All rights reserved.