(+)-2,2'-diphenyl-2,2'-dithiobisacetic acid | 4695-07-2

• 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: (+)-2,2'-diphenyl-2,2'-dithiobisacetic acid
• 英文别名: meso-bis-(phenyl-carboxy-methyl)-disulfide；2,2'-diphenyl-2,2'-disulfanediyl-di-acetic acid；(R,R)-(-)-2,2'-diphenyl-2,2'-dithiobisacetic acid；(2R,2'R')-2,2'-diphenyl-2,2'-disulfanediyl-di-acetic acid；(2R,2'R')-2,2'-Diphenyl-2,2'-disulfandiyl-di-essigsaeure；Bis-((R)-carboxy-phenyl-methyl)-disulfid；(+)-Dithio-bis-phenylessigsaeure
• CAS: 4695-07-2；16201-54-0；53318-27-7；53318-28-8
• 化学式: C₁₆H₁₄O₄S₂
• 分子量: 334.417
• InChiKey: PNIYMNCESWXSCO-ZIAGYGMSSA-N

物化性质

• 熔点：
  208-209 °C
• 沸点：
  503.9±50.0 °C(Predicted)
• 密度：
  1.425±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  22.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  74.6
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  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

文献信息

• Fredga, Acta Chemica Scandinavica (1947), 1950, vol. 4, p. 1309
  作者：Fredga

  DOI：——

  日期：——
• Ringdahl, Bjoern; Craig, J. Cymerman; Fredga, Arne, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1981, vol. 35, # 7, p. 467 - 472
  作者：Ringdahl, Bjoern、Craig, J. Cymerman、Fredga, Arne、Bonner, William A.

  DOI：——

  日期：——