2β-<(4-carboxy-1,2,3-triazol-1-yl)methyl>-2α-methylpenam-3α-carboxylic acid 1,1-dioxide | 89785-79-5

• 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: 2β-<(4-carboxy-1,2,3-triazol-1-yl)methyl>-2α-methylpenam-3α-carboxylic acid 1,1-dioxide
• 英文别名: (2S,3S,5R)-3-[(4-carboxytriazol-1-yl)methyl]-3-methyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid；(2S,3S,5R)-3-[(4-carboxytriazol-1-yl)methyl]-3-methyl-4,4,7-trioxo-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• CAS: 89785-79-5
• 化学式: C₁₁H₁₂N₄O₇S
• 分子量: 344.305
• InChiKey: ADEXHPOEPYTHKD-FYBVGQRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  168
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  p-nitrobenzyl 2β-<<4-<<(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-<(4-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

文献信息

• US4562073A
  申请人：——

  公开号：US4562073A

  公开（公告）日：1985-12-31
• 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
  作者：Ronald G. Micetich、Samarendra N. Maiti、Paul Spevak、Tse W. Hall、Shigeru Yamabe、Naobumi Ishida、Motoaki Tanaka、Tomio Yamazaki、Akira Nakai、Kazuo Ogawa

  DOI：10.1021/jm00391a032

  日期：1987.8

  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.