(6R,7R)-4-methoxybenzyl 8-oxo-3-(((2-oxo-2H-chromen-7-yl)oxy)methyl)-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | 1450821-66-5

• 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)-4-methoxybenzyl 8-oxo-3-(((2-oxo-2H-chromen-7-yl)oxy)methyl)-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• 英文别名: (4-methoxyphenyl)methyl (6R,7R)-8-oxo-3-[(2-oxochromen-7-yl)oxymethyl]-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 1450821-66-5
• 化学式: C₃₃H₂₈N₂O₈S
• 分子量: 612.66
• InChiKey: PTAYDCXQQGAOPO-QLWXXVCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  146
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (6R,7R)-4-methoxybenzyl 8-oxo-3-(((2-oxo-2H-chromen-7-yl)oxy)methyl)-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 在 苯甲醚 、 三氟乙酸 作用下， 反应 0.5h， 以37%的产率得到(6R,7R)-8-oxo-3-(((2-oxo-2H-chromen-7-yl)oxy)methyl)-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Assay Platform for Clinically Relevant Metallo-β-lactamases

  摘要：

  Metallo-beta-lactamases (MBLs) are a growing threat to the use of almost all clinically used beta-lactam antibiotics. The identification of broad-spectrum MBL inhibitors is hampered by the lack of a suitable screening platform, consisting of appropriate substrates and a set of clinically relevant MBLs. We report procedures for the preparation of a set of clinically relevant metallo-beta-lactamases (i.e., NDM-1 (New Delhi MBL), IMP-1 (Imipenemase), SPM-1 (Sao Paulo MBL), and VIM-2 (Verona integron-encoded MBL)) and the identification of suitable fluorogenic substrates (umbelliferone-derived cephalosporins). The fluorogenic substrates were compared to chromogenic,substrates (CENTA, nitrocefin, and imipenem), showing improved sensitivity and kinetic parameters. The efficiency of the fluorogenic substrates was exemplified by inhibitor screening, identifying 4- chloroisoquinolinols as potential pan MBL inhibitors.

  DOI：

  10.1021/jm400769b
• 作为产物：
  描述：

  7-苯乙酰氨基-3-氯甲基-4-头孢烷酸对甲氧基苄酯 在 potassium carbonate 、 sodium iodide 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 6.0h， 生成 (6R,7R)-4-methoxybenzyl 8-oxo-3-(((2-oxo-2H-chromen-7-yl)oxy)methyl)-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
  参考文献：
  名称：

  Assay Platform for Clinically Relevant Metallo-β-lactamases

  摘要：

  Metallo-beta-lactamases (MBLs) are a growing threat to the use of almost all clinically used beta-lactam antibiotics. The identification of broad-spectrum MBL inhibitors is hampered by the lack of a suitable screening platform, consisting of appropriate substrates and a set of clinically relevant MBLs. We report procedures for the preparation of a set of clinically relevant metallo-beta-lactamases (i.e., NDM-1 (New Delhi MBL), IMP-1 (Imipenemase), SPM-1 (Sao Paulo MBL), and VIM-2 (Verona integron-encoded MBL)) and the identification of suitable fluorogenic substrates (umbelliferone-derived cephalosporins). The fluorogenic substrates were compared to chromogenic,substrates (CENTA, nitrocefin, and imipenem), showing improved sensitivity and kinetic parameters. The efficiency of the fluorogenic substrates was exemplified by inhibitor screening, identifying 4- chloroisoquinolinols as potential pan MBL inhibitors.

  DOI：

  10.1021/jm400769b

文献信息

• A fluorogenic probe using a catalytic reaction for the detection of trace intracellular zinc
  作者：Ippei Takashima、Yohei Inoue、Nobuyuki Matsumoto、Akira Takagi、Kensuke Okuda

  DOI：10.1039/d0cc05315e

  日期：——

  A reaction-based fluorescent probe with cephem scaffold has been applied for signal amplification system to detect trace intracellular zinc.

  一种基于反应的头孢菌素骨架荧光探针已被应用于信号放大系统，用于检测微量细胞内锌。
• 一种检测结核分枝杆菌β-内酰胺酶的探针化 合物、制备方法、一种荧光探针
  申请人：中国科学院苏州生物医学工程技术研究所

  公开号：CN110105377B

  公开（公告）日：2021-08-24

  本发明公开了一种检测结核分枝杆菌β‑内酰胺酶的探针化合物，由生物素部分、头孢类结构和发光部分三个部分构成。本发明还公开了上述所述探针化合物的制备方法和一种荧光探针。包括本发明制备得到的探针化合物作为检测结核分枝杆菌β‑内酰胺酶的荧光探针，通过所述探针分子与结核分枝杆菌β‑内酰胺酶作用释放出发光部分，其中有未参与反应的探针分子通过其生物素部分和亲和素作用除去未反应探针分子，这时通过检测发光部分的含量，从而可获得β‑内酰胺酶的数据和特性，可用来检测结核分枝杆菌，提高检测灵敏度。本发明的探针化合物具有易于使用、快速检测、低成本且灵敏度高的优点。
• JP2022031028A
  申请人：——

  公开号：——

  公开（公告）日：——
• Assay Platform for Clinically Relevant Metallo-β-lactamases
  作者：Sander S. van Berkel、Jürgen Brem、Anna M. Rydzik、Ramya Salimraj、Ricky Cain、Anil Verma、Raymond J. Owens、Colin W. G. Fishwick、James Spencer、Christopher J. Schofield

  DOI：10.1021/jm400769b

  日期：2013.9.12

  Metallo-beta-lactamases (MBLs) are a growing threat to the use of almost all clinically used beta-lactam antibiotics. The identification of broad-spectrum MBL inhibitors is hampered by the lack of a suitable screening platform, consisting of appropriate substrates and a set of clinically relevant MBLs. We report procedures for the preparation of a set of clinically relevant metallo-beta-lactamases (i.e., NDM-1 (New Delhi MBL), IMP-1 (Imipenemase), SPM-1 (Sao Paulo MBL), and VIM-2 (Verona integron-encoded MBL)) and the identification of suitable fluorogenic substrates (umbelliferone-derived cephalosporins). The fluorogenic substrates were compared to chromogenic,substrates (CENTA, nitrocefin, and imipenem), showing improved sensitivity and kinetic parameters. The efficiency of the fluorogenic substrates was exemplified by inhibitor screening, identifying 4- chloroisoquinolinols as potential pan MBL inhibitors.