8-oxo-3-((4-(3-oxo-3H-benzo[f]chromene-2-carboxamido)phenylthio)methyl)-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid | 1422520-72-6

• 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: 8-oxo-3-((4-(3-oxo-3H-benzo[f]chromene-2-carboxamido)phenylthio)methyl)-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• 英文别名: (6R,7R)-8-oxo-3-[[4-[(3-oxobenzo[f]chromene-2-carbonyl)amino]phenyl]sulfanylmethyl]-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS: 1422520-72-6
• 化学式: C₃₄H₂₅N₃O₇S₃
• 分子量: 683.786
• InChiKey: JPARAOKFMNMODE-AKGWNBJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  47
• 可旋转键数：
  9
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  221
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  8-oxo-3-((4-(3-oxo-3H-benzo[f]chromene-2-carboxamido)phenylthio)methyl)-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 在 metallo-β-lactamase CcrA 作用下， 以 aq. buffer 为溶剂， 生成 、 (R)-2-[(R)-Carboxy-(2-thiophen-2-yl-acetylamino)-methyl]-5-methylene-5,6-dihydro-2H-[1,3]thiazine-4-carboxylic acid
  参考文献：
  名称：

  Novel fluorescent cephalosporins: Synthesis, antimicrobial activity and photodynamic inactivation of antibiotic resistant bacteria

  摘要：

  Two novel fluorescent cephalosporins, TCA and TBCA, were synthesized and characterized by H-1 NMR, C-13 NMR, UV-vis, and fluorescence spectroscopies. Biological activity assays demonstrated that TCA inactivated a Klebsiella pneumonia strain that expressed extended-spectrum beta-lactamases. Incubation of 6 mu M TCA with K. pneumonia cultures resulted in cell death for 84% of the cells after 126 J/cm(2) of light irradiation. In vitro, TCA exhibited a MIC = 0.5 mu g/mL with Staphylococcus aureus. Kinetic evaluation revealed that TCA and TBCA were substrates for B1 and B3 subclass metallo-beta-lactamases. TBCA exhibited stronger binding affinities to the Gram-positive bacterial strains MRSA1, MRSA2, and S. aureus with value of 2.95-6.59 mu M per 10(8) cells/mL. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.11.019
• 作为产物：
  描述：

  2-噻吩乙酰氯 在 N-甲基吗啉 、 potassium trimethylsilonate 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 苯酚 作用下， 以 二氯甲烷 、 氯仿 、 乙腈 为溶剂， 反应 19.0h， 生成 8-oxo-3-((4-(3-oxo-3H-benzo[f]chromene-2-carboxamido)phenylthio)methyl)-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Novel fluorescent cephalosporins: Synthesis, antimicrobial activity and photodynamic inactivation of antibiotic resistant bacteria

  摘要：

  Two novel fluorescent cephalosporins, TCA and TBCA, were synthesized and characterized by H-1 NMR, C-13 NMR, UV-vis, and fluorescence spectroscopies. Biological activity assays demonstrated that TCA inactivated a Klebsiella pneumonia strain that expressed extended-spectrum beta-lactamases. Incubation of 6 mu M TCA with K. pneumonia cultures resulted in cell death for 84% of the cells after 126 J/cm(2) of light irradiation. In vitro, TCA exhibited a MIC = 0.5 mu g/mL with Staphylococcus aureus. Kinetic evaluation revealed that TCA and TBCA were substrates for B1 and B3 subclass metallo-beta-lactamases. TBCA exhibited stronger binding affinities to the Gram-positive bacterial strains MRSA1, MRSA2, and S. aureus with value of 2.95-6.59 mu M per 10(8) cells/mL. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.11.019

文献信息

• Novel fluorescent cephalosporins: Synthesis, antimicrobial activity and photodynamic inactivation of antibiotic resistant bacteria
  作者：Jian-Min Xiao、Lei Feng、Li-Sheng Zhou、Hui-Zhou Gao、Yi-Lin Zhang、Ke-Wu Yang

  DOI：10.1016/j.ejmech.2012.11.019

  日期：2013.1

  Two novel fluorescent cephalosporins, TCA and TBCA, were synthesized and characterized by H-1 NMR, C-13 NMR, UV-vis, and fluorescence spectroscopies. Biological activity assays demonstrated that TCA inactivated a Klebsiella pneumonia strain that expressed extended-spectrum beta-lactamases. Incubation of 6 mu M TCA with K. pneumonia cultures resulted in cell death for 84% of the cells after 126 J/cm(2) of light irradiation. In vitro, TCA exhibited a MIC = 0.5 mu g/mL with Staphylococcus aureus. Kinetic evaluation revealed that TCA and TBCA were substrates for B1 and B3 subclass metallo-beta-lactamases. TBCA exhibited stronger binding affinities to the Gram-positive bacterial strains MRSA1, MRSA2, and S. aureus with value of 2.95-6.59 mu M per 10(8) cells/mL. (C) 2012 Elsevier Masson SAS. All rights reserved.