10-(4-Hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-3-methyl-1H,10H-pyrano[4,3-b] chromen-1-ones from a pseudo-multicomponent reaction and evaluation of their antioxidant activity |
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Authors: | Liza Saher Malika Makhloufi-Chebli Leila Dermeche Samia Dermeche Baya Boutemeur-Khedis Cherifa Rabia Maamar Hamdi Artur MS Silva |
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Institution: | 1. Lab. de Physique Chimie des Materiaux (LPCM), Département de Chimie, Faculté des Sciences, Université Mouloud Mammeri, 15000, Tizi Ouzou, Algeria;2. Lab. de Chimie Organique Appliquée (Groupe Hétérocycles), Faculté de Chimie, Université des Sciences et de la Technologie Houari Boumediène, BP 32, El-Alia, 16111, Bab-Ezzouar, Alger, Algeria;3. Lab. de Chimie du Gaz Naturel, Faculté de Chimie, Université des Sciences et de la Technologie Houari Boumediène, BP 32, El-Alia, 16111, Bab-Ezzouar, Alger, Algeria;4. Lab. de Microbiologie, Département de Biologie, Faculté des Sciences, Université Mouloud Mammeri, 15000, Tizi Ouzou, Algeria;5. Department of Chemistry & QOPNA, University of Aveiro, 3810-193, Aveiro, Portugal |
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Abstract: | A series of novel 10-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-3-methyl-1H,10H-pyrano4,3-b]chromen-1-ones were synthesized by a pseudo-three-component reaction of 4-hydroxy-6-methyl-2-oxo-2H-pyran-2-one (TAL) with 2-hydroxyarylaldehydes using different acids as catalysts and solvents. The approach relies on a regioselective cascade reaction involving two molar equiv of the TAL iteratively acting as active methylene in a Knoevenagel condensation and in a Michael addition. The antioxidant activity of the synthesized compounds were determined using the DPPH scavenging assay, being the results dependent on the nature and number of chromone substituents. The compound bearing an ortho-dihydroxy (catechol) moiety showed excellent activity at lower concentrations, while derivatives bearing alkoxy groups as substituents present pro-oxidant activity. |
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Keywords: | Pyranyl-pyranochromenes Multicomponent reactions Knoevenagel condensation Michael addition Antioxidant and pro-oxidant activity |
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