4-allyl-2-methoxyphenyl-β-D-lactoside | 1443214-49-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-allyl-2-methoxyphenyl-β-D-lactoside
• CAS: 1443214-49-0
• 化学式: C₂₂H₃₂O₁₂
• 分子量: 488.489
• InChiKey: ZVXGAGPCOANGCH-LUOIICGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.57
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  187.76
• 氢给体数：
  7.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  4-allyl-2-methoxyphenyl-(2,3,6,2',3',4',6'-hepta-O-acetyl-β-D-lactoside) 在 potassium methanolate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以50%的产率得到4-allyl-2-methoxyphenyl-β-D-lactoside
  参考文献：
  名称：

  Synthesis and in vitro evaluation of antifungal and cytotoxic activities of eugenol glycosides

  摘要：

  Six eugenol glycosides were prepared in order to assess their antifungal activity against Candida species. They were synthesized by glycosylation of eugenol with the appropriate glycosyl bromides followed by deacetylation with sodium methoxide in methanol and were evaluated in vitro for their antifungal activity through a Mueller-Hinton broth microdilution method. The peracetyl glycoside (derivative 4) was the most promising one since it was able to inhibit growth of C. albicans, C. tropicalis and C. glabrata with IC50 values much lower than that of the prototype eugenol. Derivative 4 showed to be 160.0 and 3.4 times more potent than eugenol and fluconazole, respectively, against C. glabrata with low cytotoxity (selectivity index of 45). Moreover, it was possible to verify the positive effect of gluco configuration and lipophilicity on antifungal activity, since glucose peracetyl derivatives were more active than the free sugars of galacto configuration.

  DOI：

  10.1007/s00044-013-0669-2