(6R)-3-acetoxymethyl-8-oxo-7t-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid | 10390-44-0

• 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)-3-acetoxymethyl-8-oxo-7t-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• 英文别名: 7β-(2-phenoxy-acetylamino)-cephalosporanic acid；7-phenoxyacetamidocephalosporanic acid；7(2-Phenoxyacetamido)cephalosporanic acid；(6R,7R)-3-(Acetyloxymethyl)-8-oxo-7-[(2-phenoxyacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS: 10390-44-0
• 化学式: C₁₈H₁₈N₂O₇S
• 分子量: 406.416
• InChiKey: WJJYDNKVEGMTBM-RHSMWYFYSA-N

物化性质

• 沸点：
  759.7±60.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 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)-3-acetoxymethyl-8-oxo-7t-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 在 四(三苯基膦)钯 吡啶 、 盐酸 、 sodium hydroxide 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 乙酸酐 、 焦磷酸硫胺素 、 碳酸氢钠 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 2-carboxyl-7-phenoxyacetamido-5-sulfoxide-2-cephem-3-methyl 3-methyl-4-oxo-imidazo[5,1-d][1,2,3,5]tetrazin-8-carboxylate
  参考文献：
  名称：

  Synthesis and antibacterial activity of dual-action agents of a β-lactam antibiotic with cytotoxic agent mitozolomide or temozolomide

  摘要：

  Dual-action agents 5a-f and 12a-f. a beta-lactam antibiotic combined with a cytotoxic agent. mitozolomide (Meto) or temozolomide (Temo). were synthesised. The antibacterial activity (MICs) of the dual-action agents has been determined against a panel of bacteria including several beta-lactamase producing strains. The tests showed 5a-f active against the non-p-lactamase producing methicillin sensitive Staphylococcus aureus (MSSA) strains. however, little synergistic effect between the P-lactam and the cytotoxic agent was observed. 12a-f demonstrated some synergistic effect against bacteria. 12a. in particular. is active against ampicillin resistant (beta-lactamase-producing) strains of Serratia marcescens. (C) 2002 Published by editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01331-9
• 作为产物：
  描述：

  (6R)-3-acetoxymethyl-8-oxo-7t-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester 在 水 、 氢气 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 (6R)-3-acetoxymethyl-8-oxo-7t-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  TMSI与头孢菌素酯的反应

  摘要：

  使用TMSI可以从3-乙酰氧基-和3-氨基甲酰基甲基类似物直接合成3-碘甲基头孢菌素酯。也可以使用TMSI介导的化学方法将头孢菌素钠“一锅”转化为C-3杂环取代的头孢菌素。

  DOI：

  10.1016/s0040-4039(01)82025-6

文献信息

• Optically-Detectable Enzyme Substrates and Their Method of Use
  申请人：Life Technologies Corporation

  公开号：US20160139135A1

  公开（公告）日：2016-05-19

  The present invention relates to compounds that are substrates for an enzyme, and upon reaction with the enzyme provide a detectable response, such as an optically detectable response. In particular, the compounds have utility in detecting the presence of a β-lactamase in a sample. In addition to the compounds, methods are disclosed for analyzing a sample for the presence of a β-lactmase, for example, as an indicator of expression of a nucleic acid sequence including a sequence coding for a β-lactmase. Kits are disclosed that include the disclosed compounds and additional components, for example, cells, antibodies, a β-lactmase or instructions for using the components in an assay.

  本发明涉及一种酶底物化合物，与酶反应后产生可检测的响应，例如光学可检测的响应。具体而言，这些化合物在检测样品中β-内酰胺酶的存在方面具有实用性。除了这些化合物外，还公开了用于分析样品中β-内酰胺酶存在的方法，例如，作为表达包括编码β-内酰胺酶序列的核酸序列的指示器。还公开了包括这些化合物和额外组分的试剂盒，例如细胞、抗体、β-内酰胺酶或使用这些组分进行检测的说明书。
• Optically-detectable enzyme substrates and their method of use
  申请人：Corry Boon Schuyler

  公开号：US20050227309A1

  公开（公告）日：2005-10-13

  The present invention relates to compounds that are substrates for an enzyme, and upon reaction with the enzyme provide a detectable response, such as an optically detectable response. In particular, the compounds have utility in detecting the presence of a β-lactamase in a sample. In addition to the compounds, methods are disclosed for analyzing a sample for the presence of a β-lactmase, for example, as an indicator of expression of a nucleic acid sequence including a sequence coding for a β-lactmase. Kits are disclosed that include the disclosed compounds and additional components, for example, cells, antibodies, a β-lactmase or instructions for using the components in an assay.

  本发明涉及一种酶底物化合物，与酶反应后产生可检测的响应，例如光学可检测的响应。特别是，这些化合物在检测样品中β-内酰胺酶的存在方面具有实用性。除了这些化合物外，还公开了用于分析样品中β-内酰胺酶存在的方法，例如，作为包括编码β-内酰胺酶序列的核酸序列表达的指示物。还公开了包括上述化合物和额外组分的试剂盒，例如细胞、抗体、β-内酰胺酶或使用这些组分进行检测的说明。
• OPTICALLY-DETECTABLE ENZYME SUBSTRATES AND THEIR METHOD OF USE
  申请人：CORRY Schuyler Boon

  公开号：US20090047692A1

  公开（公告）日：2009-02-19

  The present invention relates to compounds that are substrates for an enzyme, and upon reaction with the enzyme provide a detectable response, such as an optically detectable response. In particular, the compounds have utility in detecting the presence of a β-lactamase in a sample. In addition to the compounds, methods are disclosed for analyzing a sample for the presence of a β-lactmase, for example, as an indicator of expression of a nucleic acid sequence including a sequence coding for a β-lactmase. Kits are disclosed that include the disclosed compounds and additional components, for example, cells, antibodies, a β-lactmase or instructions for using the components in an assay.

  本发明涉及一种酶底物化合物，经过与该酶的反应后提供可检测的响应，例如光学可检测响应。特别是，这些化合物在检测样品中β-内酰胺酶的存在方面具有实用性。除了这些化合物，还揭示了一种分析样品中β-内酰胺酶存在的方法，例如，作为包括编码β-内酰胺酶的核酸序列的表达的指示器。还揭示了包括上述化合物和其他组分的试剂盒，例如细胞、抗体、β-内酰胺酶或使用这些组分进行检测的说明。
• Chemistry of cephalosporin antibiotics. XVII. Functionalization of deacetcephalosporin. Conversion of penicillin into cephalosporin
  作者：J. Alan Webber、Earle M. Van Heyningen、Robert T. Vasileff

  DOI：10.1021/ja01048a061

  日期：1969.9
• Dual-action cephalosporins: cephalosporin 3'-quaternary ammonium quinolones
  作者：Harry A. Albrecht、George Beskid、James G. Christenson、Joanne W. Durkin、Virve Fallat、Nafsika H. Georgopapadakou、Dennis D. Keith、Frederick M. Konzelmann、Ellen R. Lipschitz

  DOI：10.1021/jm00106a031

  日期：1991.2

  When cephalosporins exert their biological activity by reacting with bacterial enzymes, opening of the beta-lactam ring can lead to expulsion of the 3'-substituent. A series of cephalosporins was prepared in which antibacterial quinolones were linked to the 3'-position through a quaternary nitrogen. Like the 3'-ester-linked dual-action cephalosporins reported earlier, these compounds demonstrated a broad spectrum of antibacterial activity derived from cephalosporin-like and quinolone-like components, suggesting a dual mode of action.