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Research Articles

One-pot synthesis of polyhydroquinoline-1,2,3-triazole hybrids in deep eutectic solvent as anti-leishmanial agents and molecular modeling studies

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Pages 4834-4850 | Received 07 Apr 2023, Accepted 02 Jun 2023, Published online: 16 Jun 2023
 

Abstract

The novel hybrids with 1,2,3-triazole and polyhydroquinoline scaffolds were successfully synthesized by multicomponent reaction of propargyloxybenzaldehyde, 1,3-cyclohexadione, ethylacetoacetate and ammonium acetate followed through click reaction in the presence of deep eutectic solvent ChCl/ZnCl2 as an efficient catalyst. Their anti-leishmanial activity was evaluated against amastigote and promastigote forms of L. tropica, L. major, and two different species of L. infantum. Furthermore, to determine the cytotoxicity of the hybrids, they were evaluated against the murine macrophage cell line J774.A1. Based on the results, three hybrids showed the highest antileishmanial activity. However, they revealed low cytotoxicity. Hybrid 6j was the most potent compound against both the forms of all leishmanial types, with IC50 = 13.5 and 11.9 µg/mL for L. major, 37.5 and 25 µg/mL for L. tropica, 17.5 and 20 µg/mL for L. infantum (MCAN/IR//96/LON49) and 35.5 and 30 µg/mL for L. infantum (MCAN/ES/98/LIM-877), respectively. Finally, molecular docking and molecular dynamics simulations were also performed to identify possible mechanism antileishmanial activity.

Communicated by Ramaswamy H. Sarma

Disclosure statement

The authors declare that there is no conflict of interest.

Additional information

Funding

Supports of this project by Ardabil University of Medical Sciences are welcomed. The funding Number is IR.ARUMS.REC.1400.132.

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