2,6-dimethyl-4-(3'-O-benzyl-1',2'-O-isopropylidene-β-L-threo-pentofuranos-4'-yl)-1-(4-methylphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester | 1229579-92-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2,6-dimethyl-4-(3'-O-benzyl-1',2'-O-isopropylidene-β-L-threo-pentofuranos-4'-yl)-1-(4-methylphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester
• CAS: 1229579-92-3
• 化学式: C₃₂H₃₇NO₈
• 分子量: 563.648
• InChiKey: AJAYSRBTJRXDRF-KWYVSSJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.79
• 重原子数：
  41.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  乙烷,三氯氟- 、 乙酰乙酸甲酯 、 3-O-苄基-1,2-O-异亚丙基-Alpha-D-木质二醛糖 在 四丁基硫酸氢铵 作用下， 以 二乙二醇 为溶剂， 反应 6.0h， 以78%的产率得到2,6-dimethyl-4-(3'-O-benzyl-1',2'-O-isopropylidene-β-L-threo-pentofuranos-4'-yl)-1-(4-methylphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl 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