3-(2-chloroethyl)-4-oxo-imidazo[5,1-d]-1,2,3,5-tetrazine-8-carboxylic acid N-hydroxysuccinimide ester | 473988-44-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑四嗪类
• 英文名称: 3-(2-chloroethyl)-4-oxo-imidazo[5,1-d]-1,2,3,5-tetrazine-8-carboxylic acid N-hydroxysuccinimide ester
• 英文别名: (2,5-Dioxopyrrolidin-1-yl) 3-(2-chloroethyl)-4-oxoimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylate
• CAS: 473988-44-2
• 化学式: C₁₁H₉ClN₆O₅
• 分子量: 340.683
• InChiKey: JJWUXISHFJMKNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  127
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  氨苄西林 、 3-(2-chloroethyl)-4-oxo-imidazo[5,1-d]-1,2,3,5-tetrazine-8-carboxylic acid N-hydroxysuccinimide ester 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以61%的产率得到α-[(3-(2-chloroethyl)-4-oxo-imidazo[5,1-d]-1,2,3,5-tetrazine-8-carboxyl)aminobenzyl]penicillin
  参考文献：
  名称：

  Synthesis and antibacterial activity of dual-action agents of a β-lactam antibiotic with cytotoxic agent mitozolomide or temozolomide

  摘要：

  Dual-action agents 5a-f and 12a-f. a beta-lactam antibiotic combined with a cytotoxic agent. mitozolomide (Meto) or temozolomide (Temo). were synthesised. The antibacterial activity (MICs) of the dual-action agents has been determined against a panel of bacteria including several beta-lactamase producing strains. The tests showed 5a-f active against the non-p-lactamase producing methicillin sensitive Staphylococcus aureus (MSSA) strains. however, little synergistic effect between the P-lactam and the cytotoxic agent was observed. 12a-f demonstrated some synergistic effect against bacteria. 12a. in particular. is active against ampicillin resistant (beta-lactamase-producing) strains of Serratia marcescens. (C) 2002 Published by editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01331-9
• 作为产物：
  描述：

  米托唑胺 在 硫酸 、 N,N'-二环己基碳二亚胺 、 sodium nitrite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 3-(2-chloroethyl)-4-oxo-imidazo[5,1-d]-1,2,3,5-tetrazine-8-carboxylic acid N-hydroxysuccinimide ester
  参考文献：
  名称：

  Synthesis and antibacterial activity of dual-action agents of a β-lactam antibiotic with cytotoxic agent mitozolomide or temozolomide

  摘要：

  Dual-action agents 5a-f and 12a-f. a beta-lactam antibiotic combined with a cytotoxic agent. mitozolomide (Meto) or temozolomide (Temo). were synthesised. The antibacterial activity (MICs) of the dual-action agents has been determined against a panel of bacteria including several beta-lactamase producing strains. The tests showed 5a-f active against the non-p-lactamase producing methicillin sensitive Staphylococcus aureus (MSSA) strains. however, little synergistic effect between the P-lactam and the cytotoxic agent was observed. 12a-f demonstrated some synergistic effect against bacteria. 12a. in particular. is active against ampicillin resistant (beta-lactamase-producing) strains of Serratia marcescens. (C) 2002 Published by editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01331-9