5-iodo-3-(2-aminopyrimidin-5-yl)isoxazole | 862096-01-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-iodo-3-(2-aminopyrimidin-5-yl)isoxazole
• 英文别名: 5-(5-Iodo-1,2-oxazol-3-yl)pyrimidin-2-amine
• CAS: 862096-01-3
• 化学式: C₇H₅IN₄O
• 分子量: 288.047
• InChiKey: DZPFESDBFPCVEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-iodo-3-(2-aminopyrimidin-5-yl)isoxazole 、 在 bis-triphenylphosphine-palladium(II) chloride 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以62%的产率得到(1S,2R,5S,7R,8R,9R,11R,13R,14R)-9-[3-[3-(2-aminopyrimidin-5-yl)-1,2-oxazol-5-yl]prop-2-ynoxy]-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-5-fluoro-1,5,7,9,11,13-hexamethyl-3,17-dioxa-15-azabicyclo[12.3.0]heptadecane-4,6,12,16-tetrone
  参考文献：
  名称：

  Synthesis and antibacterial activity of 6-O-(heteroaryl-isoxazolyl)propynyl 2-fluoro ketolides

  摘要：

  Macrolide antibiotics are widely prescribed for the treatment of respiratory tract infections; however, the increasing prevalence of macrolide-resistant pathogens is a public health concern. Therefore, the development of new macrolide derivatives with activities against resistant pathogens is urgently needed. A series of novel 6-O-(heteroaryl-isoxazolyl)propynyl 2-fluoro ketolides has been synthesized from erythromycin A. These compounds have shown very promising in vitro and in vivo antibacterial activities against key respiratory pathogens including erythromycin-susceptible/resistant strains. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.092
• 作为产物：
  描述：

  2-氨基-5-嘧啶甲醛 在 吡啶 、 N-氯代丁二酰亚胺 、 盐酸羟胺 、 碳酸氢钠 作用下， 以 乙醇 、 水 、 乙酸乙酯 为溶剂， 反应 18.75h， 生成 5-iodo-3-(2-aminopyrimidin-5-yl)isoxazole
  参考文献：
  名称：

  Synthesis and antibacterial activity of 6-O-(heteroaryl-isoxazolyl)propynyl 2-fluoro ketolides

  摘要：

  Macrolide antibiotics are widely prescribed for the treatment of respiratory tract infections; however, the increasing prevalence of macrolide-resistant pathogens is a public health concern. Therefore, the development of new macrolide derivatives with activities against resistant pathogens is urgently needed. A series of novel 6-O-(heteroaryl-isoxazolyl)propynyl 2-fluoro ketolides has been synthesized from erythromycin A. These compounds have shown very promising in vitro and in vivo antibacterial activities against key respiratory pathogens including erythromycin-susceptible/resistant strains. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.092