(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 | 1262837-61-5

• 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)-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
• 英文别名: (6R,7R)-8-oxo-3-((2-oxo-2H-chromen-7-yloxy)methyl)-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid；CDC-1；(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-carboxylic acid
• CAS: 1262837-61-5
• 化学式: C₂₅H₂₀N₂O₇S
• 分子量: 492.509
• InChiKey: GSAFHPBIKKAXIT-ZJSXRUAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  148
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (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 在 次氯酸叔丁酯 、 三异丙基硅烷 、 水 、 potassium carbonate 、 三氟乙酸 、 三氟乙酸酐 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 aq. phosphate buffer 、 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 4.58h， 生成 (6R,7S)-7-methoxy-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：

  [EN] BETA-LACTAMASE SUBSTRATES AND METHODS OF THEIR USE FOR THE DIAGNOSIS OF TUBERCULOSIS
  [FR] SUBSTRATS DE BÊTA-LACTAMASES ET LEURS PROCÉDÉS D'UTILISATION DANS LE DIAGNOSTIC DE LA TUBERCULOSE

  摘要：

  β-内酰胺酶底物及其使用方法，用于检测β-内酰胺酶诊断结核病。

  公开号：

  WO2013173519A1
• 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 、 苯甲醚 、 三氟乙酸 、 sodium iodide 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 6.5h， 生成 (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

文献信息

• BETA-LACTAMASE SUBSTRATES AND METHODS OF THEIR USE FOR THE DIAGNOSIS OF TUBERCULOSIS
  申请人：The Texas A&M University System

  公开号：US20150167048A1

  公开（公告）日：2015-06-18

  β-Lactamase substrates and methods for using the substrates to detect β-lactamase diagnose tuberculosis.

  β-内酰胺酶底物及其用于检测β-内酰胺酶诊断结核病的方法。
• USE OF BACTERIAL BETA-LACTAMASE FOR IN VITRO DIAGNOSTICS AND IN VIVO IMAGING, DIAGNOSTICS AND THERAPEUTICS
  申请人：Cirillo Jeffrey D.

  公开号：US20130164221A1

  公开（公告）日：2013-06-27

  Provided herein are methods for detecting, quantifying, differentiating, diagnosing and imaging pathogenic bacteria or condition associated therewith using substrates for bacterial enzymes. Fluorescent, luminescent or colorimetric signals emitted by substrates or enzyme products in the presence of the bacteria are compared to controls to detect and locate the pathogenic bacteria. Provided is a method for screening therapeutic agents to treat the pathophysiological conditions by measuring a signal emitted from the substrates or products in the presence and absence of the potential therapeutic agent and a diagnostic method for detecting a mycobacterial infection in a subject by contacting biological samples with a substrate and imaging for signals emitted from a mycobacterial beta-lactamase product. Also provided are fluorogenic substrates or substrates comprising a colored dye or a chemical reagent effective to induce a color or pH change.
• US9138490B2
  申请人：——

  公开号：US9138490B2

  公开（公告）日：2015-09-22
• US9441261B2
  申请人：——

  公开号：US9441261B2

  公开（公告）日：2016-09-13
• US9677112B2
  申请人：——

  公开号：US9677112B2

  公开（公告）日：2017-06-13