(R)-2-(acetylthio)-2-phenylacetic acid

• 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: (R)-2-(acetylthio)-2-phenylacetic acid
• 英文别名: (2R)-2-acetylsulfanyl-2-phenylacetic acid
• 化学式: C₁₀H₁₀O₃S
• 分子量: 210.254
• InChiKey: GCBDFXPLCNQIFE-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  79.7
• 氢给体数：
  1
• 氢受体数：
  4

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(R)-2-mercapto-3-phenylacetic acid (R-thiomandelic acid)	16201-51-7	C8H8O2S	168.216

反应信息

• 作为反应物：
  描述：

  (R)-2-(acetylthio)-2-phenylacetic acid 在 碘 作用下， 以 水 、 乙腈 为溶剂， 生成 (+)-2,2'-diphenyl-2,2'-dithiobisacetic acid
  参考文献：
  名称：

  Thiol-Containing Metallo-β-Lactamase Inhibitors Resensitize Resistant Gram-Negative Bacteria to Meropenem

  摘要：

  The prevalence of infections caused by metallo-beta-lactamase (MBL) expressing Gram-negative bacteria has grown at an alarming rate in recent years. Despite the fact that MBLs can deactivate virtually all beta-lactam antibiotics, there are as of yet no approved drugs available that inhibit their activity. We here examine the ability of previously reported thiol-based MBL inhibitors to synergize with meropenem and cefoperazone against a panel of Gram-negative carbapenem-resistant isolates expressing different beta-lactamases. Among the compounds tested, thiomandelic acid 3 and 2-mercapto-3-phenylpropionic acid 4 were found to efficiently potentiate the activity of meropenem, especially against an imipenemase (IMP) producing strain of K. pneumoniae. In light of the zinc-dependent hydrolytic mechanism employed by MBLs, biophysical studies using isothermal titration calorimetry were also performed, revealing a correlation between the synergistic activity of thiols 3 and 4 and their zinc-binding ability with measured K-d values of 9.8 and 20.0 mu M, respectively.

  DOI：

  10.1021/acsinfecdis.7b00094
• 作为产物：
  描述：

  (S)-(+)-扁桃酸 、 硫代乙酸 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以48%的产率得到(2S)-(acetylthio)(phenyl)ethanoic acid
  参考文献：
  名称：

  借助Mitsunobu型试剂在某些α-羟基酸的硫代乙酰化反应中形成α-内酯的证据

  摘要：

  （S-扁桃酸，（S）-乳酸和（S）-2-羟基-3-苯基丙酸在偶氮二羧酸二异丙酯和三苯基膦的盐存在下与硫代乙酸反应生成α-（乙酰硫基）- （S）-扁桃酸主要与构型反应，而（S）-乳酸和（S）-2-羟基-3-苯基丙酸主要与转化反应，α-内酯中间体的参与非常可能。

  DOI：

  10.1002/recl.19871061006

文献信息

• Thiol-Containing Metallo-β-Lactamase Inhibitors Resensitize Resistant Gram-Negative Bacteria to Meropenem
  作者：Kamaleddin Haj Mohammad Ebrahim Tehrani、Nathaniel I. Martin

  DOI：10.1021/acsinfecdis.7b00094

  日期：2017.10.13

  The prevalence of infections caused by metallo-beta-lactamase (MBL) expressing Gram-negative bacteria has grown at an alarming rate in recent years. Despite the fact that MBLs can deactivate virtually all beta-lactam antibiotics, there are as of yet no approved drugs available that inhibit their activity. We here examine the ability of previously reported thiol-based MBL inhibitors to synergize with meropenem and cefoperazone against a panel of Gram-negative carbapenem-resistant isolates expressing different beta-lactamases. Among the compounds tested, thiomandelic acid 3 and 2-mercapto-3-phenylpropionic acid 4 were found to efficiently potentiate the activity of meropenem, especially against an imipenemase (IMP) producing strain of K. pneumoniae. In light of the zinc-dependent hydrolytic mechanism employed by MBLs, biophysical studies using isothermal titration calorimetry were also performed, revealing a correlation between the synergistic activity of thiols 3 and 4 and their zinc-binding ability with measured K-d values of 9.8 and 20.0 mu M, respectively.
• Evidence for α-lactone formation in the thioacetylation of some α-hydroxy acids with the aid of <i>Mitsunobu</i> -type reagent
  作者：Bert Strijtveen、Richard M. Kellogg

  DOI：10.1002/recl.19871061006

  日期：——

  (S-Mandelic acid, (S)-lactic acid, and (S)-2-hydroxy-3-phenylpropionic acid react with thioacetic acid in the presence of the salt of diisopropyl azodicarboxylate and triphenylphosphine to give the α-(acetylthio)-substituted products. (S)-Mandelic acid reacts with predominant retention of configuration whereas (S)-lactic acid and (S)-2-hydroxy-3-phenylpropionic acid react predominantly with inversion

  （S-扁桃酸，（S）-乳酸和（S）-2-羟基-3-苯基丙酸在偶氮二羧酸二异丙酯和三苯基膦的盐存在下与硫代乙酸反应生成α-（乙酰硫基）- （S）-扁桃酸主要与构型反应，而（S）-乳酸和（S）-2-羟基-3-苯基丙酸主要与转化反应，α-内酯中间体的参与非常可能。