diphenylmethyl (2S,3R,5R)-3-(hydroxyimino)methyl-3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate | 188249-95-8

• 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: diphenylmethyl (2S,3R,5R)-3-(hydroxyimino)methyl-3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate
• CAS: 188249-95-8
• 化学式: C₂₁H₂₀N₂O₆S
• 分子量: 428.466
• InChiKey: BSNJBSGIISATGB-LMNJBCLMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.89
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  113.34
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  diphenylmethyl (2S,3R,5R)-3-(hydroxyimino)methyl-3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 5.5h， 以23%的产率得到sodium (2S,3R,5R)-3-(hydroxyimino)methyl-3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of penam sulfones as inhibitors of β-lactamases

  摘要：

  The chemical synthesis of a series of new penam sulfone derivatives bearing a 2 beta-substituted-oxyimino and -hydrazone substituents, their beta-lactamase inhibitory properties against selected enzymes representing class A and C beta-lactamases are reported. The oxime containing pertain sulfones strongly inhibited the Escherichia coli TEM-1 and Klebsiella pneumoniae cefotaximase (CTX-1) enzymes, but moderately inhibited the Pseudomonas aeruginosa 46012 cephalosporinase; while the 2 beta-substituted-hydrazone derivatives were generally less active against these enzymes. Furthermore, most of the inhibitors enhanced the antibacterial activities of piperacillin (PIP) and ceftazidime (CAZ) particularly against TEM-1 and CTX-1 producing bacterial strains. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.020
• 作为产物：
  描述：

  diphenylmethyl (2S,3R,5R)-3-formyl-3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate 在 吡啶 、 盐酸羟胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 5.5h， 以35%的产率得到diphenylmethyl (2S,3R,5R)-3-(hydroxyimino)methyl-3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of penam sulfones as inhibitors of β-lactamases

  摘要：

  The chemical synthesis of a series of new penam sulfone derivatives bearing a 2 beta-substituted-oxyimino and -hydrazone substituents, their beta-lactamase inhibitory properties against selected enzymes representing class A and C beta-lactamases are reported. The oxime containing pertain sulfones strongly inhibited the Escherichia coli TEM-1 and Klebsiella pneumoniae cefotaximase (CTX-1) enzymes, but moderately inhibited the Pseudomonas aeruginosa 46012 cephalosporinase; while the 2 beta-substituted-hydrazone derivatives were generally less active against these enzymes. Furthermore, most of the inhibitors enhanced the antibacterial activities of piperacillin (PIP) and ceftazidime (CAZ) particularly against TEM-1 and CTX-1 producing bacterial strains. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.020