6β-bromo-6α-(1-hydroxyethyl)-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid benzyhydryl ester | 483340-25-6

• 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: 6β-bromo-6α-(1-hydroxyethyl)-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid benzyhydryl ester
• 英文别名: 6β-bromo-6α-(1-hydroxyethyl)-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid benzyhydryl ester
• CAS: 483340-25-6
• 化学式: C₂₃H₂₄BrNO₆S
• 分子量: 522.417
• InChiKey: DAODUAFRIJAOLE-HWTIFENNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  100.98
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6β-bromo-6α-(1-hydroxyethyl)-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid benzyhydryl ester 在 苯甲醚 、 三氟乙酸 作用下， 反应 3.0h， 以34%的产率得到6β-bromo-6α-(1-hydroxyethyl)-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of 6-bromo-6-substituted penicillanic acid derivatives as β-lactamase inhibitors

  摘要：

  The synthesis of a selected set of 6-bromopenicillanic acid derivatives with an additional C6 substituent is reported. All these substances were tested as inhibitors of class A and C beta-lactamase enzymes derived from Escherichia coli (TEM-1) and E. cloacae (P99). As 6-(1-hydroxyethyl) derivatives 4c and 6c were found to be weak beta-lactamase inhibitors, they were further investigated in combination with amoxicillin against a series of beta-lactamase-producing bacterial strains. Some structure-activity relationships are discussed. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0014-827x(02)01261-2
• 作为产物：
  描述：

  diphenylmethyl 6,6-dibromopenicillanate 在 甲基溴化镁 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 20.66h， 生成 6β-bromo-6α-(1-hydroxyethyl)-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid benzyhydryl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of 6-bromo-6-substituted penicillanic acid derivatives as β-lactamase inhibitors

  摘要：

  The synthesis of a selected set of 6-bromopenicillanic acid derivatives with an additional C6 substituent is reported. All these substances were tested as inhibitors of class A and C beta-lactamase enzymes derived from Escherichia coli (TEM-1) and E. cloacae (P99). As 6-(1-hydroxyethyl) derivatives 4c and 6c were found to be weak beta-lactamase inhibitors, they were further investigated in combination with amoxicillin against a series of beta-lactamase-producing bacterial strains. Some structure-activity relationships are discussed. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0014-827x(02)01261-2