(R)-5,5,8-Trioxo-3-phenyl-7-[1-pyridin-2-yl-meth-(Z)-ylidene]-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester | 371207-77-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-5,5,8-Trioxo-3-phenyl-7-[1-pyridin-2-yl-meth-(Z)-ylidene]-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
• 英文别名: benzhydryl (6R,7Z)-5,5,8-trioxo-3-phenyl-7-(pyridin-2-ylmethylidene)-5lambda6-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate；benzhydryl (6R,7Z)-5,5,8-trioxo-3-phenyl-7-(pyridin-2-ylmethylidene)-5λ6-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 371207-77-1
• 化学式: C₃₂H₂₄N₂O₅S
• 分子量: 548.619
• InChiKey: WKGQMAMICIBQJS-VYGJAXMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  40
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-5,5,8-Trioxo-3-phenyl-7-[1-pyridin-2-yl-meth-(Z)-ylidene]-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 在 苯甲醚 、 三氟乙酸 作用下， 生成 (R)-5,5,8-Trioxo-3-phenyl-7-[1-pyridin-2-yl-meth-(Z)-ylidene]-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Cephalosporin-derived inhibitors of β-Lactamase. Part 4: The C3 substituent

  摘要：

  New C3-substituted beta-lactamase inhibitors were prepared and evaluated against representative class A and class C enzymes. It was possible to improve simultaneous inhibitory activity of both classes of serine hydrolase. Other inhibitors showed high selectivity for either the class C cephalosporinases or the class A penicillinases. This represents the first time that cephalosporin-derived inhibitors have demonstrated selectivity for the class A beta-lactamases. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00205-6
• 作为产物：
  描述：

  3-羟基头孢 在 吡啶 、 tris(dibenzylideneacetone)dipalladium (0) 、 亚硝酸异丙酯 、 五氯化磷 、 potassium tert-butylate 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 、 三氟乙酸 、 lithium iodide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.5h， 生成 (R)-5,5,8-Trioxo-3-phenyl-7-[1-pyridin-2-yl-meth-(Z)-ylidene]-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
  参考文献：
  名称：

  Coupling Reactions of Cephalosporin Sulfones:  A Stable 3-Stannylated Cephem

  摘要：

  [GRAPHICS]The first stable 3-metalated cephalosporin is reported and shown to be an excellent synthetic precursor to a number of prospective beta -lactamase inhibitors.

  DOI：

  10.1021/ol016142v

文献信息

• Coupling Reactions of Cephalosporin Sulfones:  A Stable 3-Stannylated Cephem
  作者：John D. Buynak、Lakshminarayana Vogeti、Hansong Chen

  DOI：10.1021/ol016142v

  日期：2001.9.1

  [GRAPHICS]The first stable 3-metalated cephalosporin is reported and shown to be an excellent synthetic precursor to a number of prospective beta -lactamase inhibitors.
• Cephalosporin-derived inhibitors of β-Lactamase. Part 4: The C3 substituent
  作者：John D. Buynak、Lakshminarayana Vogeti、Venkata Ramana Doppalapudi、George Martin Solomon、Hansong Chen

  DOI：10.1016/s0960-894x(02)00205-6

  日期：2002.6

  New C3-substituted beta-lactamase inhibitors were prepared and evaluated against representative class A and class C enzymes. It was possible to improve simultaneous inhibitory activity of both classes of serine hydrolase. Other inhibitors showed high selectivity for either the class C cephalosporinases or the class A penicillinases. This represents the first time that cephalosporin-derived inhibitors have demonstrated selectivity for the class A beta-lactamases. (C) 2002 Elsevier Science Ltd. All rights reserved.