(E)-3-(3,4,5-trimethoxyphenyl)-1-(3,(6)7-dimethyl-1,4-dioxyquinoxalin-2-yl)prop-2-en-1-one | 1301603-30-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-(3,4,5-trimethoxyphenyl)-1-(3,(6)7-dimethyl-1,4-dioxyquinoxalin-2-yl)prop-2-en-1-one
• CAS: 1301603-30-4
• 化学式: C₂₂H₂₂N₂O₆
• 分子量: 410.426
• InChiKey: CCBUYGMTMKWMDF-VQHVLOKHSA-N

反应信息

• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 、 1-(3,7-dimethyl-1,4-dioxyquinoxaline-2-yl)ethanone 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 (E)-3-(3,4,5-trimethoxyphenyl)-1-(3,(6)7-dimethyl-1,4-dioxyquinoxalin-2-yl)prop-2-en-1-one
  参考文献：
  名称：

  Flavonoid‐Quinoxaline Hybrid Compounds as Cathepsin Inhibitors Against Fascioliasis

  摘要：

  Fasciola hepatica is a parasitic trematode that infects livestock animals and humans, causing significant health and economic burdens worldwide. The extensive use of anthelmintic drugs has led to the emergence of resistant parasite strains, posing a threat to treatment success. The complex life cycle of the liver fluke, coupled with limited funding and research interest, have hindered progress in drug discovery. Our group has been working in drug development against this parasite using cathepsin proteases as molecular targets, finding promising compound candidates with in vitro and in vivo efficacy. Here, we evaluated hybrid molecules that combine two chemotypes, chalcones and quinoxaline 1,4‐di‐ N‐oxides, previously found to inhibit F. hepatica cathepsin Ls and tested their in vitro activity with the isolated targets and the parasites in culture. These molecules proved to be good cathepsin inhibitors and to kill the juvenile parasites at micromolar concentrations. Also, we performed molecular docking studies to analyze the compounds‐cathepsins interface, finding that the best inhibitors interact at the active site cleft and contact the catalytic dyad and residues belonging to the substrate binding pockets. We conclude that the hybrid compounds constitute promising scaffolds for the further development of new fasciolicidal compounds.

  DOI：

  10.1002/cmdc.202400305