(6R,7R)-2-(allyloxy)carbonyl-7-(2-thienyl)acetamido-3-cephem-3-methyl 3-methyl-4-oxoimidazo[5,1-d][1,2,3,5]tetrazin-8-carboxylate | 473988-52-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (6R,7R)-2-(allyloxy)carbonyl-7-(2-thienyl)acetamido-3-cephem-3-methyl 3-methyl-4-oxoimidazo[5,1-d][1,2,3,5]tetrazin-8-carboxylate
• 英文别名: prop-2-enyl (6R,7R)-3-[(3-methyl-4-oxoimidazo[5,1-d][1,2,3,5]tetrazine-8-carbonyl)oxymethyl]-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylate
• CAS: 473988-52-2
• 化学式: C₂₃H₂₁N₇O₇S₂
• 分子量: 571.594
• InChiKey: ICFLACAVTGEPQW-RMRANGLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  218
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (6R,7R)-2-(allyloxy)carbonyl-7-(2-thienyl)acetamido-3-cephem-3-methyl 3-methyl-4-oxoimidazo[5,1-d][1,2,3,5]tetrazin-8-carboxylate 在 四(三苯基膦)钯 焦磷酸硫胺素 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 2-carboxyl-5-sulfoxide-7-(2-thienyl)acetamido-2-cephem-3-methyl 3-methyl-4-oxoimidazo[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：

  头孢噻吩 在 吡啶 、 盐酸 、 sodium hydroxide 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 乙酸酐 、 碳酸氢钠 、 N,N-二异丙基乙胺 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 1.0h， 生成 (6R,7R)-2-(allyloxy)carbonyl-7-(2-thienyl)acetamido-3-cephem-3-methyl 3-methyl-4-oxoimidazo[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

文献信息

• METHODS AND COMPOUNDS FOR DETECTING BETA-LACTAMASE ACTIVITY
  申请人：XING Bengang

  公开号：US20090275065A1

  公开（公告）日：2009-11-05

  The present invention relates to compounds for and a method of detecting beta-lactamase activity in a sample. The sample is contacted with a nanoparticulate tag. The nanoparticulate tag comprises a metal or a combination of metals, or it comprises a nanotube of a metal, boron nitride and/or carbon. The respective metal is capable of forming one of a covalent bond, a coordinative bond and a non-covalent interaction with a thio or a seleno group. The sample is contacted with a compound of one of general formulas (I)-(III) and (VII)-(IX). At least one beta-lactam moiety of the compound is cleaved by the beta-lactamase activity in the sample. As a result a cleavage moiety Z-A-Z, Z-A-Z-R 15 , Z-A-Z-R 16 , Z-A-Z-R 17 , Z-A-Z-R 18 or Z-G-N(R 8 )R 9 is released that is immobilised on the surface of the nanoparticulate tag by a covalent bond via a Z atom. The presence of beta-lactamase activity is determined based on the presence of the cleavage moiety immobilized onto the surface of the nanoparticulate tag.

  本发明涉及一种用于检测样品中β-内酰胺酶活性的化合物和方法。样品与纳米颗粒标记物接触。纳米颗粒标记物包括金属或金属组合，或者包括金属、硼氮化物和/或碳的纳米管。所述金属能够与硫或硒基团形成共价键、配位键或非共价相互作用之一。样品与一般式(I)-(III)和(VII)-(IX)中的化合物接触。化合物中的至少一个β-内酰胺基团被样品中的β-内酰胺酶活性切割。结果释放出一个通过Z原子通过共价键固定在纳米颗粒标记物表面上的切割基团Z-A-Z、Z-A-Z-R15、Z-A-Z-R16、Z-A-Z-R17、Z-A-Z-R18或Z-G-N(R8)R9。通过检测固定在纳米颗粒标记物表面上的切割基团来确定β-内酰胺酶活性的存在。
• US8802387B2
  申请人：——

  公开号：US8802387B2

  公开（公告）日：2014-08-12
• US9476087B2
  申请人：——

  公开号：US9476087B2

  公开（公告）日：2016-10-25
• Synthesis and antibacterial activity of dual-action agents of a β-lactam antibiotic with cytotoxic agent mitozolomide or temozolomide
  作者：Yongfeng Wang、Peter Lambert、Linxiang Zhao、Danni Wang

  DOI：10.1016/s0223-5234(01)01331-9

  日期：2002.4

  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.