2,6-dimethyl-4-(3'-O-benzyl-1',2'-O-isopropylidene-β-L-threo-pentofuranos-4'-yl)-1-(4-fluorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester | 1229579-94-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 2,6-dimethyl-4-(3'-O-benzyl-1',2'-O-isopropylidene-β-L-threo-pentofuranos-4'-yl)-1-(4-fluorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester
• CAS: 1229579-94-5
• 化学式: C₃₃H₃₈FNO₈
• 分子量: 595.665
• InChiKey: JQBXYPQRWFHOOR-SVYISMGTSA-N

物化性质

• 熔点：
  132-135 °C
• 沸点：
  650.7±55.0 °C(predicted)
• 密度：
  1.28±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  43.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  92.76
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  乙酰乙酸乙酯 、 3-O-苄基-1,2-O-异亚丙基-Alpha-D-木质二醛糖 、 4-氟苯胺 在 四丁基硫酸氢铵 作用下， 以 二乙二醇 为溶剂， 反应 10.0h， 以76%的产率得到2,6-dimethyl-4-(3'-O-benzyl-1',2'-O-isopropylidene-β-L-threo-pentofuranos-4'-yl)-1-(4-fluorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  Synthesis and molecular docking studies of 1-phenyl-4-glycosyl-dihydropyridines as potent antileishmanial agents

  摘要：

  A series of 1-phenyl-4-glycosyl-dihydropyridines (4-17 and 19-21) were prepared by the one pot multicomponent reaction of glcosyl aldehyde, beta-keto compounds and aniline or substituted aniline in the presence of TBAHS as catalyst. The compounds were screened in vitro and in vivo for their antileishmanial activities. Most of the compounds exhibited moderate to good activity against amastigotes and promastigotes of Leishmania donovani. The compounds 4, 11, 12, 13, and 17 exhibited potent in vivo activity with selectivity index (SI) values 743-18 93. Molecular docking studies with these compounds revealed L. donovani PTRI as the possible target to show antileishmanial activities.

  DOI：

  10.1016/j.ejmech.2010.02.018