benzhydryl (2S,3S,5R,6R)-6-(hydroxymethyl)-3-methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate | 229489-93-4

• 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,6R)-6-(hydroxymethyl)-3-methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• 英文别名: benzhydryl (2S,3S,5R,6R)-6-(hydroxymethyl)-3-methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 229489-93-4
• 化学式: C₂₄H₂₄N₄O₆S
• 分子量: 496.544
• InChiKey: RSCRNPCQNVJFQJ-BTDSVWAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  140
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  benzhydryl (2S,3S,5R,6R)-6-(hydroxymethyl)-3-methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 在 碳酸氢钠 、 间甲酚 作用下， 以80%的产率得到sodium;(2S,3S,5R,6R)-6-(hydroxymethyl)-3-methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4lambda6-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：

  benzhydryl (2S,3S,5R)-6-bromo-6-(hydroxymethyl)-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 作用下， 以85%的产率得到benzhydryl (2S,3S,5R,6R)-6-(hydroxymethyl)-3-methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4lambda6-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

文献信息

• 6-(1-Hydroxyalkyl)penam sulfone derivatives as inhibitors of class A and class C β-lactamases II
  作者：Panayota Bitha、Zhong Li、Gerardo D. Francisco、Youjun Yang、Peter J. Petersen、Eileen Lenoy、Yang-I Lin

  DOI：10.1016/s0960-894x(99)00107-9

  日期：1999.4

  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.