4-hydroxy-6-methyl-3-nitropyridin-2(1H)-one 2-hydroxyethylamine | 1447823-67-7

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 4-hydroxy-6-methyl-3-nitropyridin-2(1H)-one 2-hydroxyethylamine
• CAS: 1447823-67-7
• 化学式: C₂H₇NO*C₆H₆N₂O₄
• 分子量: 231.208
• InChiKey: ASRRCORHUYRRTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.77
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  142.48
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  4-羟基-6-甲基-3-硝基-2-吡啶醇 、 C.I.酸性橙108 以 乙醇 为溶剂， 以93%的产率得到4-hydroxy-6-methyl-3-nitropyridin-2(1H)-one 2-hydroxyethylamine
  参考文献：
  名称：

  Ultrasound-assisted improvement of drug solubility: a simple and useful method for the formation of salts from 4-hydroxy-6-methyl-3-nitropyridin-2(1H)-one

  摘要：

  The low aqueous solubility of drug-like compounds has been described as one of the main problems causing the failure of new chemical entities in medicinal chemistry programmes. This paper describes our efforts to overcome lack of solubility and to produce a novel template protocol for forming salts of poorly soluble compounds. We prepared a series of 4-hydroxy-6-methyl-3-nitropyridin-2(1H)-one amine salts by using ultrasound irradiation. The poorly water-soluble molecule 4-hydroxy-6-methyl-3-nitropyridin-2(1H)-one was recently described as an inhibitor of the Mycobacterium tuberculosis orotate phosphoribosyltransferase enzyme. Salts of this molecule were prepared in 88-98 % yield from a mixture of 4-hydroxy-6-methyl-3-nitropyridin-2(1H)-one with primary and secondary amines (dimethylamine, diethylamine, dipropylamine, ethanolamine, 2-amino-2-methyl-1,3-propanediol, d-threoninol, pyrrolidine and piperidine) after ultrasound irradiation. The main advantages of this method are a significant reduction in reaction times and the use of a renewable solvent as a reaction medium. Thus the compounds are obtained after irradiation for 8 min in ethanol.

  DOI：

  10.1007/s00706-013-0948-0