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Coumarin-based Trisubstituted Methanes as Potent Anthelmintic: Synthesis, Molecular Docking and in vitro Efficacy

Abstract

A series of coumarin-based trisubstituted methanes (TRSMs) having uracil scaffold was synthesised employing a green, chromatography-free, and a highly efficient sonochemical multicomponent reaction of diverse aldehydes with 1,3-dimethyl-6-aminouracil and 4-hydroxy-coumarin in the presence of a catalytic amount of DABCO at room temperature and tested their anthelmintic efficacy against helminth parasites, Raillietina echinobothrida and Syphacia obvelata. Some of the TRSMs with substituents in the para position of the phenyl ring showed excellent anthelmintic activity in comparison to the commonly used drugs such as albendazole and praziquantel. The docking study revealed the binding interaction of all the optimized compounds with several amino acid residues in the active site of β-tubulin. The compounds showing good docking score with β-tubulin showed comparable anthelmintic activity experimentally as well.

Graphic Abstract

A series of coumarin based trisubstituted methanes (TRSMs) were synthesized and they showed excellent anthelmintic properties in comparison to conventional benzimidazoles.

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Funding

This research did not receive any specific grant from funding agency in the public, commercial, or not-for-profit sectors.

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Correspondence to Ghanashyam Bez.

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Basumatary, G., Dhar, E.D., Das, D. et al. Coumarin-based Trisubstituted Methanes as Potent Anthelmintic: Synthesis, Molecular Docking and in vitro Efficacy. J Chem Sci 132, 40 (2020). https://doi.org/10.1007/s12039-020-1737-z

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Keywords

  • Coumarin-based TRSMs
  • Sonochemical MCR
  • Anthelmintic
  • Raillietina echinobothrida
  • Syphacia obvelata
  • Molecular docking