3-Hydroxymethyl-7β-phenylacetamido-ceph-2-em-4ξ-carbonsaeure | 7629-50-7

• 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: 3-Hydroxymethyl-7β-phenylacetamido-ceph-2-em-4ξ-carbonsaeure
• 英文别名: (6R)-3-hydroxymethyl-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2ξ-carboxylic acid；(6R,7R)-3-(hydroxymethyl)-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid
• CAS: 7629-50-7
• 化学式: C₁₆H₁₆N₂O₅S
• 分子量: 348.379
• InChiKey: AFOWTLRTDLDXLT-ILWWEHDPSA-N

物化性质

• 沸点：
  779.7±60.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  132
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-Hydroxymethyl-7β-phenylacetamido-ceph-2-em-4ξ-carbonsaeure 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 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 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (6R,7R)-2-(allyloxy)carbonyl-7-phenylacetamido-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
• 作为产物：
  描述：

  头孢洛仑 在 吡啶 、 盐酸 、 sodium hydroxide 、 乙酸酐 作用下， 以 水 为溶剂， 生成 3-Hydroxymethyl-7β-phenylacetamido-ceph-2-em-4ξ-carbonsaeure
  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

• Cephem Derivatives and a process for their manufacture
  申请人：KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY

  公开号：EP0301257A2

  公开（公告）日：1989-02-01

  Cephem derivatives of the formula and physiologically acceptable salts thereof, a process for their manufacture, pharmaceutical preparations containing them and the intermediates of the formula

  Cephem衍生物的公式及其生理上可接受的盐，其制备方法，含有它们的药物制剂以及该公式的中间体。
• Cephalosporanic acids. Part IV. 7-Acylamidoceph-2-em-4-carboxylic acids
  作者：J. D. Cocker、S. Eardley、G. I. Gregory、M. E. Hall、A. G. Long

  DOI：10.1039/j39660001142

  日期：——

  The combined action of bases and acid anhydrides on 7-acylamidocephalosporanic acids, and the action of bases on their esters, set up equilibria in which the corresponding Δ2-isomers predominate. The isomerisation represents a prototropic shift probably favoured by the sulphur atom in the dihydrothiazine ring. The acetoxy-group in the Δ2-compounds can be replaced by nucleophiles.

  的碱和酸酐7-acylamidocephalosporanic酸的联合作用，以及碱基对它们的酯的动作，设置了其中相应Δ均衡2 -异构体占优势。异构化表示质子交换，这可能是二氢噻嗪环中的硫原子所促进的。的乙酰氧基团在Δ 2 -化合物可以通过亲核试剂代替。