diphenylmethyl (6R,7R)-3-(4-nitrophenoxycarbonyloxy)methyl-7-(2-thienylacetamido)-Δ³-cephem-4-carboxylate | 135508-68-8

• 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: diphenylmethyl (6R,7R)-3-(4-nitrophenoxycarbonyloxy)methyl-7-(2-thienylacetamido)-Δ³-cephem-4-carboxylate
• 英文别名: diphenylmethyl 7β-(2-thienylacetamido)-3-((4-nitrophenoxy)-carbonyl-oxymethyl)-cephem-4-carboxylate；3-[[[(4-nitrophenoxy)carbonyl]oxy]methyl]-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester；benzhydryl (6R,7R)-3-[(4-nitrophenoxy)carbonyloxymethyl]-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 135508-68-8
• 化学式: C₃₄H₂₇N₃O₉S₂
• 分子量: 685.735
• InChiKey: SQWDRVKLFQWANB-AKGWNBJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  48
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  211
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  diphenylmethyl (6R,7R)-3-(4-nitrophenoxycarbonyloxy)methyl-7-(2-thienylacetamido)-Δ³-cephem-4-carboxylate 在 苯甲醚 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Conjoint molecules of cephalosporins and aminoglycosides

  摘要：

  A general synthetic route to conjoint molecules of cephalosporins and aminoglycosides is described. These molecules were designed as potential substrates for bacterial beta -lactamases, enzymes that hydrolyze the beta -lactam bond of cephalosporins. Hydrolysis of the beta -lactam bond was expected to release the Clo-appended aminoglycoside. Since beta -lactamases are sequestered in the periplasmic space of gram-negative bacteria, this sequence of events would liberate aminoglycoside inside such bacteria. It is expected that such local delivery of aminoglycosides would circumvent the inherent toxicity of aminoglycosides that occurs during systemic exposure within the mammalian host.

  DOI：

  10.1002/1521-4184(200109)334:8/9<295::aid-ardp295>3.0.co;2-3
• 作为产物：
  描述：

  (6R-反式)-3-(羟基甲基)-8-氧代-7-(2-噻吩基乙酰氨基)-5-硫杂-1-氮杂双环[4.2.0]辛-2-烯-2-羧酸 在 吡啶 、 4-二甲氨基吡啶 、 mercury(II) oxide 作用下， 以 二氯甲烷 、 正戊烷 为溶剂， 反应 7.0h， 生成 diphenylmethyl (6R,7R)-3-(4-nitrophenoxycarbonyloxy)methyl-7-(2-thienylacetamido)-Δ³-cephem-4-carboxylate
  参考文献：
  名称：

  [EN] FLUOROGENIC BETA-LACTAMASE SUBSTRATE AND ASSOCIATED DETECTION METHOD
  [FR] SUBSTRAT DE BÊTA-LACTAMASE FLUOROGÉNIQUE ET MÉTHODE DE DÉTECTION ASSOCIÉE

  摘要：

  这项发明涉及用于检测β-内酰胺酶型酶活性的探针。具体而言，该发明涉及用于检测具有催化活性的β-内酰胺酶存在的新型荧光基底物，以及使用这种基底物的检测方法。

  公开号：

  WO2021105512A1

文献信息

• [EN] FLUOROGENIC BETA-LACTAMASE SUBSTRATE AND ASSOCIATED DETECTION METHOD<br/>[FR] SUBSTRAT DE BÊTA-LACTAMASE FLUOROGÉNIQUE ET MÉTHODE DE DÉTECTION ASSOCIÉE
  申请人：MOLSID

  公开号：WO2021105512A1

  公开（公告）日：2021-06-03

  This invention relates to probes for the detection of β-lactamase-type enzymatic activity. In particular, the invention relates to novel fluorogenic substrates for detecting the presence of a catalytically active β-lactamase and a detection method using such substrates.

  这项发明涉及用于检测β-内酰胺酶型酶活性的探针。具体而言，该发明涉及用于检测具有催化活性的β-内酰胺酶存在的新型荧光基底物，以及使用这种基底物的检测方法。
• Synthesis and Total 1H- and 13C-NMR Assignment of Cephem Derivatives for Use in ADEPT Approaches
  作者：Lorena Blau、Renato Menegon、Elizabeth Ferreira、Antonio Ferreira、Elisangela Boffo、Leila Tavares、Vladimir Heleno、Man-Chin Chung

  DOI：10.3390/molecules13040841

  日期：——

  We report the synthesis and total NMR characterization of 5-thia-1-azabicyclo-[4.2.0]oct-2-ene-2-carboxylic acid-3-[[[(4’’-nitrophenoxy)carbonyl]oxy]-methyl]-8-oxo-7-[(2-thienyloxoacetyl)amino]-diphenylmethyl ester-5-dioxide (5), a new cephalosporin derivative. This compound can be used as the carrier of a wide range of drugs containing an amino group. The preparation of the intermediate product,

  我们报告了 5-thia-1-azabicyclo-[4.2.0]oct-2-ene-2-carboxy-3-[[[(4''-nitrophenoxy)carbonyl]oxy]-[[[(4''-nitrophenoxy)carbonyl]oxy]-的合成和总核磁共振表征甲基]-8-oxo-7-[(2-thienyloxoacetyl)amino]-diphenylmethylester-5-dioxide (5)，一种新的头孢菌素衍生物。该化合物可用作多种含有氨基的药物的载体。中间产物5-硫杂-1-氮杂双环[4.2.0]oct-2-烯-2-羧酸-3-[4-(6-甲氧基喹啉-8-基氨基)戊基氨基甲酸甲酯]-8-的制备oxo-7-[(2-thienyloxoacetyl)amino]-diphenylmethylester-5-dioxide (6)，以及抗疟伯氨喹前药 5-thia-1-azabicyclo[4
• A Practical Synthetic Method for 3-(N,N-Disubstituted Carbamoyloxy)methyl Cephems without Generating the .DELTA.2-Isomers.
  作者：Shigeto NEGI、Motosuke YAMANAKA、Yuki KOMATSU、Akihiko TSURUOKA、Atsushi KAMADA、Itaru TSUKADA、Yoshimasa MACHIDA

  DOI：10.1248/cpb.43.1031

  日期：——

  E1101, a new oral caphalosporin, has a (N, N-dimethylcarbamoyloxy)methyl group at the C-3 position of the cephem nucleus. The previous methods for manufacturing 3-(N, N-disubstituted carbamoyloxy)methyl cephems generate various amounts of intractable Δ2 isomers as by-products. In this report, we describe a new, practical synthetic method for cephems of this type without generating Δ2 isomers, via 7-acylamino-3-(4-nitrophenoxy-carbonyloxy)methyl-Δ3-cephem-4-carboxylic acid (5) as a key intermediate.

  E1101 是一种新型口服头孢菌素，在头孢菌素核的 C-3 位上有一个（N，N-二甲基氨基甲酰氧基）甲基。以往生产 3-（N，N-二取代氨基甲酰氧基）甲基头孢菌素的方法会产生不同数量的难以处理的Δ2 异构体作为副产品。在本报告中，我们介绍了一种以 7-酰氨基-3-(4-硝基苯氧基-碳酰氧基)甲基-Δ3-头孢-4-羧酸 (5) 为关键中间体、不产生 Δ2 异构体的新型实用头孢合成方法。
• Conjoint molecules of cephalosporins and aminoglycosides
  作者：Ioannis Grapsas、Stephen A. Lerner、Shahriar Mobashery

  DOI：10.1002/1521-4184(200109)334:8/9<295::aid-ardp295>3.0.co;2-3

  日期：2001.9

  A general synthetic route to conjoint molecules of cephalosporins and aminoglycosides is described. These molecules were designed as potential substrates for bacterial beta -lactamases, enzymes that hydrolyze the beta -lactam bond of cephalosporins. Hydrolysis of the beta -lactam bond was expected to release the Clo-appended aminoglycoside. Since beta -lactamases are sequestered in the periplasmic space of gram-negative bacteria, this sequence of events would liberate aminoglycoside inside such bacteria. It is expected that such local delivery of aminoglycosides would circumvent the inherent toxicity of aminoglycosides that occurs during systemic exposure within the mammalian host.