p-nitrobenzyl 2β-<<5-<<(p-nitrobenzyl)oxy>carbonyl>-1,2,3-triazol-1-yl>methyl>-2α-methylpenam-3α-carboxylate 1,1-dioxide | 89785-77-3

• 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: p-nitrobenzyl 2β-<<5-<<(p-nitrobenzyl)oxy>carbonyl>-1,2,3-triazol-1-yl>methyl>-2α-methylpenam-3α-carboxylate 1,1-dioxide
• 英文别名: (4-nitrophenyl)methyl (2S,3S,5R)-3-methyl-3-[[5-[(4-nitrophenyl)methoxycarbonyl]triazol-1-yl]methyl]-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate；(4-nitrophenyl)methyl (2S,3S,5R)-3-methyl-3-[[5-[(4-nitrophenyl)methoxycarbonyl]triazol-1-yl]methyl]-4,4,7-trioxo-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 89785-77-3
• 化学式: C₂₅H₂₂N₆O₁₁S
• 分子量: 614.549
• InChiKey: CZVUNPKPIUCUEL-SLSDLSHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  238
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  p-nitrobenzyl 2β-<<5-<<(p-nitrobenzyl)oxy>carbonyl>-1,2,3-triazol-1-yl>methyl>-2α-methylpenam-3α-carboxylate 1,1-dioxide 在 palladium on activated charcoal 氢气 、 碳酸氢钠 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 1.0h， 生成 2β-<(5-carboxy-1,2,3-triazol-1-yl)methyl>-2α-methylpenam-3α-carboxylic acid 1,1-dioxide
  参考文献：
  名称：

  Synthesis and .beta.-lactamase inhibitory properties of 2.beta.-[(1,2,3-triazol-1-yl)methyl]-2.alpha.-methylpenam-3.alpha.-carboxylic acid 1,1-dioxide and related triazolyl derivatives

  摘要：

  Benzhydryl 2 beta-[(1,2,3-triazol-1-yl)methyl]-2 alpha-methylpenam- 3 alpha-carboxylate 1,1-dioxide was prepared by heating benzhydryl 2 beta-(azidomethyl)-2 alpha-methylpenam-3 alpha-carboxylate 1,1-dioxide with (trimethylsilyl)acetylene. The ester group was removed by hydrogenolysis to give sodium 2 beta-[(1,2,3-triazol-1-yl)methyl]-2 alpha-methylpenam-3 alpha-carboxylate 1,1-dioxide (3i, YTR-830), which was found to be a potent inhibitor of various bacterial beta-lactamases. A series of related compounds was prepared in a similar way, and all of these compounds show excellent beta-lactamase inhibitory properties.

  DOI：

  10.1021/jm00391a032
• 作为产物：
  描述：

  p-nitrobenzyl 2β-(azidomethyl)-2α-methylpenam-3α-carboxylate 1,1-dioxide 、 (4-硝基苯基)甲基丙-2-炔酸酯 生成 p-nitrobenzyl 2β-<<5-<<(p-nitrobenzyl)oxy>carbonyl>-1,2,3-triazol-1-yl>methyl>-2α-methylpenam-3α-carboxylate 1,1-dioxide
  参考文献：
  名称：

  RONARUDO, DZEDZI, MIKEHTEHJSSYU;YAMABEH, SIGEHRU;TANAKA, MOTOAKI;KADZIYA,+

  摘要：

  DOI：

文献信息

• Penicillin derivatives and process for preparation of the same
  申请人：TAIHO PHARMACEUTICAL COMPANY LIMITED

  公开号：EP0097446A1

  公开（公告）日：1984-01-04

  A penicillin derivative represented by the following formula, and a pharmaceutically acceptable salt thereof and ester thereof: wherein R, and R2 are each the same of different and represent hydrogen atom, trialkylsilyl group, carboxyl group, carboxyl group forming a pharmaceutically acceptable salt or esterified carboxyl group, and a process for preparing the same and a β-lactamase inhibitor.

  由下式代表的青霉素衍生物，及其药学上可接受的盐和酯类：其中R，和R2各自相同或不同，代表氢原子、三烷基硅烷基、羧基、形成药学上可接受的盐的羧基或酯化羧基，以及制备该衍生物和β-内酰胺酶抑制剂的工艺。
• US4562073A
  申请人：——

  公开号：US4562073A

  公开（公告）日：1985-12-31