tert-butyl N-methyl-N-[3-[2-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolo[3,2-b]pyridin-1-yl]propyl]carbamate | 1018949-71-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: tert-butyl N-methyl-N-[3-[2-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolo[3,2-b]pyridin-1-yl]propyl]carbamate
• CAS: 1018949-71-7
• 化学式: C₂₁H₃₂N₄O₄
• 分子量: 404.509
• InChiKey: DXPAXQDWERJXMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  85.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl N-methyl-N-[3-[2-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolo[3,2-b]pyridin-1-yl]propyl]carbamate 、 二碳酸二叔丁酯 在 4-二甲氨基吡啶 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 以71%的产率得到tert-butyl 3-(2-(bis(tert-butoxycarbonyl)amino)-1H-pyrrolo[3,2-c]pyridin-1-yl)propyl(methyl)carbamate
  参考文献：
  名称：

  A novel series of parenteral cephalosporins exhibiting potent activities against both Pseudomonas aeruginosa and other Gram-negative pathogens. Part 2: Synthesis and structure–activity relationships

  摘要：

  A novel series of 7 beta-[2-(2-amino-5-chloro-thiazol-4-yl)-2(Z)-((S)-1-carboxyethoxyimino)acetamido]cephalosporins bearing various pyridinium groups at the C-3' position were synthesized and their in vitro antibacterial activities against Gram-negative pathogens including Pseudomonas aeruginosa and several Gram-positive pathogens were evaluated. Among the cephalosporins prepared, we found that a cephalosporin bearing the 2- amino-1-(3-methylamino-propyl)-1H-imidazo[4,5-b] pyridinium group at the C-3' position (8a) showed potent and well-balanced antibacterial activities against P. aeruginosa and other Gram-negative pathogens including the strains which produce class C beta-lactamase and extended spectrum beta-lactamase (ESBL). Compound 8a also showed efficacious in vivo activity and high stability against AmpC beta-lactamase. These findings indicate that 2-aminoimidazopyridinium having an aminoalkyl group at the 1-position as a C-3' side chain is suitable for cephalosporins bearing an aminochlorothiazolyl moiety and a carboxyethoxyimino moiety on the C-7 side chain. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.11.028
• 作为产物：
  描述：

  tert-butyl N-[3-[[2-(cyanomethyl)pyridin-3-yl]amino]propyl]-N-methylcarbamate 、 二碳酸二叔丁酯 在 盐酸 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 为溶剂， 反应 1.75h， 以90%的产率得到tert-butyl N-methyl-N-[3-[2-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolo[3,2-b]pyridin-1-yl]propyl]carbamate
  参考文献：
  名称：

  A novel series of parenteral cephalosporins exhibiting potent activities against both Pseudomonas aeruginosa and other Gram-negative pathogens. Part 2: Synthesis and structure–activity relationships

  摘要：

  A novel series of 7 beta-[2-(2-amino-5-chloro-thiazol-4-yl)-2(Z)-((S)-1-carboxyethoxyimino)acetamido]cephalosporins bearing various pyridinium groups at the C-3' position were synthesized and their in vitro antibacterial activities against Gram-negative pathogens including Pseudomonas aeruginosa and several Gram-positive pathogens were evaluated. Among the cephalosporins prepared, we found that a cephalosporin bearing the 2- amino-1-(3-methylamino-propyl)-1H-imidazo[4,5-b] pyridinium group at the C-3' position (8a) showed potent and well-balanced antibacterial activities against P. aeruginosa and other Gram-negative pathogens including the strains which produce class C beta-lactamase and extended spectrum beta-lactamase (ESBL). Compound 8a also showed efficacious in vivo activity and high stability against AmpC beta-lactamase. These findings indicate that 2-aminoimidazopyridinium having an aminoalkyl group at the 1-position as a C-3' side chain is suitable for cephalosporins bearing an aminochlorothiazolyl moiety and a carboxyethoxyimino moiety on the C-7 side chain. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.11.028