1-(2,3-Dihydroxy-propyl)-3-methyl-1H-quinoxalin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 1-(2,3-Dihydroxy-propyl)-3-methyl-1H-quinoxalin-2-one
• 英文别名: 1-(2,3-Dihydroxypropyl)-3-methyl-quinoxalin-2-one；1-(2,3-dihydroxypropyl)-3-methylquinoxalin-2-one
• 化学式: C₁₂H₁₄N₂O₃
• mdl: MFCD25814433
• 分子量: 234.255
• InChiKey: HTBNUKYFRVEIGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  73.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (+/-)-1-(2,3-O-isopropylidene-2,3-dihydroxyprop-1-yl)-3-methyl-1H-quinoxalin-2-one 在 溶剂黄146 作用下， 反应 2.0h， 以35%的产率得到1-(2,3-Dihydroxy-propyl)-3-methyl-1H-quinoxalin-2-one
  参考文献：
  名称：

  Synthesis and Anti-Hepatitis B Virus Activity of Some 2,3-Dihydroxyprop-1-yl Unnatural Hetaryls

  摘要：

  The sodium salts of some hetaryls of the quinoxalin-2-ones 2-4, phthalazine-1,4-dione 5, phthalazin-1-one 6, and pyridazin-6-ones 7 and 8 were alkylated with (+/-) 2,3-O-isopropylidene-1-O-(4-toluenesulfonyl)glycerol (1) to give the respective tetraseco-nucleosides 9-15. Their deisopropylidenation with 70% acetic acid in water gave the corresponding 2,3-dihydroxyprop-1-yl hetaryls 16-22. Compounds 16-22 showed varying inhibition activity against Hepatitis B virus (HBV) with low to moderate cytotoxicity, where 18 and 21 showed the highest replication inhibition and low cytotoxicity.

  DOI：

  10.1002/(sici)1521-4184(19999)332:9<327::aid-ardp327>3.0.co;2-n

文献信息

• Synthesis and Anti-Hepatitis B Virus Activity of Some 2,3-Dihydroxyprop-1-yl Unnatural Hetaryls
  作者：El Sayed H. El Ashry、Adel A.-H. Abdel-Rahman、Nagwa Rashed、Hanaa A. Rasheed

  DOI：10.1002/(sici)1521-4184(19999)332:9<327::aid-ardp327>3.0.co;2-n

  日期：1999.9

  The sodium salts of some hetaryls of the quinoxalin-2-ones 2-4, phthalazine-1,4-dione 5, phthalazin-1-one 6, and pyridazin-6-ones 7 and 8 were alkylated with (+/-) 2,3-O-isopropylidene-1-O-(4-toluenesulfonyl)glycerol (1) to give the respective tetraseco-nucleosides 9-15. Their deisopropylidenation with 70% acetic acid in water gave the corresponding 2,3-dihydroxyprop-1-yl hetaryls 16-22. Compounds 16-22 showed varying inhibition activity against Hepatitis B virus (HBV) with low to moderate cytotoxicity, where 18 and 21 showed the highest replication inhibition and low cytotoxicity.