2-Mercapto-thiazole-4-carboxylic acid dimethylamide | 189149-07-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-Mercapto-thiazole-4-carboxylic acid dimethylamide
• 英文别名: N,N-dimethyl-2-sulfanylidene-3H-1,3-thiazole-4-carboxamide
• CAS: 189149-07-3
• 化学式: C₆H₈N₂OS₂
• 分子量: 188.274
• InChiKey: JSEFYYYJWUTREO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  89.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Mercapto-thiazole-4-carboxylic acid dimethylamide 在 palladium on activated charcoal MOPS buffer 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 19.0h， 生成 (4R,5S,6S)-3-(4-Dimethylcarbamoyl-thiazol-2-ylsulfanyl)-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and biological properties of a new series of anti-MRSA β-lactams; 2-(thiazol-2-ylthio)carbapenems

  摘要：

  A series of 1 beta-methylcarbapenems containing variously C-2 substituted thiazol-2-ylthio groups were synthesized, and their in vitro anti-MRSA activity was examined. Among them, 1 beta-methyl-2-(4-arylthiazol-2-ylthio) carbapenems exhibited superior anti-MRSA activity. Introduction of a cationic moiety in the C-2 side chain not only reduced the binding to HSA but also increased the stability against DHP-I, without affecting the anti-MRSA, activity. It was also found that the distance between the cationic moiety and the carbapenem skeleton was related to the strength of HSA binding and the stability against DHP-I. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(96)00273-8
• 作为产物：
  描述：

  2-(4-Methoxy-benzylsulfanyl)-thiazole-4-carboxylic acid dimethylamide 在 三氟乙酸 作用下， 反应 10.0h， 以67%的产率得到2-Mercapto-thiazole-4-carboxylic acid dimethylamide
  参考文献：
  名称：

  Synthesis and biological properties of a new series of anti-MRSA β-lactams; 2-(thiazol-2-ylthio)carbapenems

  摘要：

  A series of 1 beta-methylcarbapenems containing variously C-2 substituted thiazol-2-ylthio groups were synthesized, and their in vitro anti-MRSA activity was examined. Among them, 1 beta-methyl-2-(4-arylthiazol-2-ylthio) carbapenems exhibited superior anti-MRSA activity. Introduction of a cationic moiety in the C-2 side chain not only reduced the binding to HSA but also increased the stability against DHP-I, without affecting the anti-MRSA, activity. It was also found that the distance between the cationic moiety and the carbapenem skeleton was related to the strength of HSA binding and the stability against DHP-I. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(96)00273-8