(6R,7R)-3-[(E)-3-[(5-chlorothiophen-3-yl)sulfonylamino]prop-1-enyl]-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | 1243262-55-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (6R,7R)-3-[(E)-3-[(5-chlorothiophen-3-yl)sulfonylamino]prop-1-enyl]-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS: 1243262-55-6
• 化学式: C₂₂H₂₀ClN₃O₆S₃
• 分子量: 554.068
• InChiKey: XLODIDJTTDHAEA-ZHBFVYIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  195
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  5-chlorothiophene-3-sulfonyl chloride 、 在 BSA 作用下， 以 二氯甲烷 为溶剂， 生成 (6R,7R)-3-[(E)-3-[(5-chlorothiophen-3-yl)sulfonylamino]prop-1-enyl]-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Propenylamide and propenylsulfonamide cephalosporins as a novel class of anti-MRSA β-lactams

  摘要：

  Novel C(3) propenylamide and propenylsulfonamide cephalosporins have been synthesized and tested for their ability to inhibit the penicillin-binding protein 2' (PBP2') from Staphylococcus epidermidis and the growth of a panel of clinically relevant bacterial species, including methicillin-resistant Staphylococcus aureus (MRSA). The most potent compounds inhibited the growth of MRSA strains with minimum inhibitory concentrations (MIC) as low as 1 mu g/mL. The structure-activity relationship revealed the potential for further optimization of this new cephalosporin class. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.05.110

文献信息

• Propenylamide and propenylsulfonamide cephalosporins as a novel class of anti-MRSA β-lactams
  作者：Jens Pohlmann、Natalya I. Vasilevich、Andrei I. Glushkov、Laurenz Kellenberger、Stuart Shapiro、Patrick Caspers、Malcolm G.P. Page、Franck Danel

  DOI：10.1016/j.bmcl.2010.05.110

  日期：2010.8

  Novel C(3) propenylamide and propenylsulfonamide cephalosporins have been synthesized and tested for their ability to inhibit the penicillin-binding protein 2' (PBP2') from Staphylococcus epidermidis and the growth of a panel of clinically relevant bacterial species, including methicillin-resistant Staphylococcus aureus (MRSA). The most potent compounds inhibited the growth of MRSA strains with minimum inhibitory concentrations (MIC) as low as 1 mu g/mL. The structure-activity relationship revealed the potential for further optimization of this new cephalosporin class. (C) 2010 Elsevier Ltd. All rights reserved.