Ionic liquid-catalyzed green protocol for multi-component synthesis of dihydropyrano[2,3-c]pyrazoles as potential anticancer scaffolds
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|Title:||Ionic liquid-catalyzed green protocol for multi-component synthesis of dihydropyrano[2,3-c]pyrazoles as potential anticancer scaffolds
|Author:||Nimbalkar, Urja D.
Seijas Vázquez, Julio Antonio
Vázquez Tato, María del Pilar
Damale, Manoj G.
Sangshetti, Jaiprakash N.
Nikalje, Anna Pratima G.
|Affiliation:||Universidade de Santiago de Compostela. Departamento de Química Orgánica
|Subject:||Ionic liquid | Multi-component synthesis | Dihydropyrano[2,3-c]pyrazoles | Anticancer activity | ADMET prediction | Molecular docking study ||
|Date of Issue:||2017
|Citation:||Nimbalkar, U.D.; Seijas, J.A.; Vazquez-Tato, M.P.; Damale, M.G.; Sangshetti, J.N.; Nikalje, A.P.G. Ionic Liquid-Catalyzed Green Protocol for Multi-Component Synthesis of Dihydropyrano[2,3-c]pyrazoles as Potential Anticancer Scaffolds. Molecules 2017, 22, 1628.
|Abstract:||A series of 6-amino-4-substituted-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles 5a–j were synthesized via one-pot, four-component condensation reactions of aryl aldehydes 1a–j, propanedinitrile (2), hydrazine hydrate (3) and ethyl acetoacetate (4) under solvent-free conditions. We report herein the use of the Brønsted acid ionic liquid (BAIL) triethylammonium hydrogen sulphate [Et3NH][HSO4] as catalyst for this multi-component synthesis. Compared with the available reaction methodology, this new method has consistent advantages, including excellent yields, a short reaction time, mild reaction conditions and catalyst reusability. Selected synthesized derivatives were evaluated for in vitro anticancer activity against four human cancer cell lines viz. melanoma cancer cell line (SK-MEL-2), breast cancer cell line(MDA-MB-231), leukemia cancer cell line (K-562) and cervical cancer cell line (HeLa). Compounds 5b, 5d, 5g, 5h and 5j exhibited promising anticancer activity against all selected human cancer cell lines, except HeLa. Molecular docking studies also confirmed 5b and 5d as good lead molecules. An in silico ADMET study of the synthesized anticancer agents indicated good oral drug-like behavior and non-toxic nature.|
|Rights:||© 2017 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/)
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