1-((2S,3S,5R)-2-Benzhydryloxycarbonyl-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]hept-3-ylmethyl)-1H-[1,2,3]triazole-4,5-dicarboxylic acid dimethyl ester | 89051-55-8

• 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: 1-((2S,3S,5R)-2-Benzhydryloxycarbonyl-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]hept-3-ylmethyl)-1H-[1,2,3]triazole-4,5-dicarboxylic acid dimethyl ester
• 英文别名: dimethyl 1-[[(2S,3S,5R)-2-benzhydryloxycarbonyl-3-methyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptan-3-yl]methyl]triazole-4,5-dicarboxylate；dimethyl 1-[[(2S,3S,5R)-2-benzhydryloxycarbonyl-3-methyl-4,4,7-trioxo-4λ6-thia-1-azabicyclo[3.2.0]heptan-3-yl]methyl]triazole-4,5-dicarboxylate
• CAS: 89051-55-8
• 化学式: C₂₇H₂₆N₄O₉S
• 分子量: 582.591
• InChiKey: VZTHLRDRGNKSCY-HEXNQTKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  172
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1-((2S,3S,5R)-2-Benzhydryloxycarbonyl-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]hept-3-ylmethyl)-1H-[1,2,3]triazole-4,5-dicarboxylic acid dimethyl ester 在 palladium on activated charcoal 氢气 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 以53 mg的产率得到sodium 2β-<<4,5-bis(methoxycatbonyl)-1,2,3-triazol-1-yl>methyl>-2α-methylpenam-3α-carboxylate 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：

  benzhydryl 2β-(azidomethyl)-2α-methylpenam-3α-carboxylate 1,1-dioxide 、 丁炔二酸二甲酯 以 苯 为溶剂， 反应 18.0h， 以0.495 g的产率得到1-((2S,3S,5R)-2-Benzhydryloxycarbonyl-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]hept-3-ylmethyl)-1H-[1,2,3]triazole-4,5-dicarboxylic acid dimethyl ester
  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

文献信息

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

  公开号：EP0097446B1

  公开（公告）日：1986-02-26
• MICETICH, R. G.;YAMABE, SHIGERU;YAMAZAKI, TOMIO;ISHIDA, NAOBUMI;ISHIZAWA,+
  作者：MICETICH, R. G.、YAMABE, SHIGERU、YAMAZAKI, TOMIO、ISHIDA, NAOBUMI、ISHIZAWA,+

  DOI：——

  日期：——
• KADZITANI, AKIRA;TANAKA, MOTOAKI;YAMADZAKI, TOMIO
  作者：KADZITANI, AKIRA、TANAKA, MOTOAKI、YAMADZAKI, TOMIO

  DOI：——

  日期：——
• JPS58225091A
  申请人：——

  公开号：JPS58225091A

  公开（公告）日：1983-12-27
• US4507239A
  申请人：——

  公开号：US4507239A

  公开（公告）日：1985-03-26