benzhydryl (2S,3S,5R)-6-bromo-6-[(1R)-1-hydroxyethyl]-3-methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate | 229489-89-8

• 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: benzhydryl (2S,3S,5R)-6-bromo-6-[(1R)-1-hydroxyethyl]-3-methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 229489-89-8
• 化学式: C₂₅H₂₅BrN₄O₆S
• 分子量: 589.467
• InChiKey: YVLNTGNRPIDSFO-JOAQKJRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.85
• 重原子数：
  37.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  131.69
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  benzhydryl (2S,3S,5R)-6-bromo-6-[(1R)-1-hydroxyethyl]-3-methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 在 三正丁基氢锡 、 碳酸氢钠 、 间甲酚 作用下， 生成 sodium;(2S,3S,5R,6R)-6-[(1R)-1-hydroxyethyl]-3-methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
  参考文献：
  名称：

  6-(1-Hydroxyalkyl)penam sulfone derivatives as inhibitors of class A and class C β-lactamases II

  摘要：

  Two stereoselective processes for the synthesis of novel 3,6-disubstituted penam sulfone derivatives were developed. One 6 beta-(l-hydroxyethyl) and four 6 beta-hydroxymethyl penam sulfone derivatives were synthesized. All four 6 beta-(hydroxymethyl)penam sulfone derivatives demonstrated good IC50 against both TEM-1 and AmpC beta-lactamases. of these, 6 beta-hydroxymethyl penam sulfone derivative 25 was the most active inhibitor which was able to restore the activity of piperacillin in vitro and in vivo against both TEM-1 and AmpC beta-lactamases producing organisms. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00107-9
• 作为产物：
  描述：

  6,6-dibromo-2,2-dimethylpenam-3-carboxylic acid 1-oxide diphenylmethyl ester 在 potassium permanganate 、 叔丁基氯化镁 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 benzhydryl (2S,3S,5R)-6-bromo-6-[(1R)-1-hydroxyethyl]-3-methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
  参考文献：
  名称：

  6-(1-Hydroxyalkyl)penam sulfone derivatives as inhibitors of class A and class C β-lactamases II

  摘要：

  Two stereoselective processes for the synthesis of novel 3,6-disubstituted penam sulfone derivatives were developed. One 6 beta-(l-hydroxyethyl) and four 6 beta-hydroxymethyl penam sulfone derivatives were synthesized. All four 6 beta-(hydroxymethyl)penam sulfone derivatives demonstrated good IC50 against both TEM-1 and AmpC beta-lactamases. of these, 6 beta-hydroxymethyl penam sulfone derivative 25 was the most active inhibitor which was able to restore the activity of piperacillin in vitro and in vivo against both TEM-1 and AmpC beta-lactamases producing organisms. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00107-9