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Synthesis and Biological Evaluation of 3-cyano-4H-chromene Derivatives Bearing Carbamate Functionality

[ Vol. 15 , Issue. 3 ]

Author(s):

Fatma Boukattaya, Amal Daoud, Fabien Boeda, Morwenna S. M. Pearson-Long, Neji Gharsallah, Adel Kadri, Philippe Bertus* and Houcine Ammar   Pages 257 - 264 ( 8 )

Abstract:


Background: 2-Aminochromene derivatives display important pharmacological properties, including mainly antibiotic and anticancer activities.

Objective: The study aims to synthesize new chromene derivatives via a new approach using Grignard reagents, for the evaluation of their antibiotic and antifungal properties.

Method: A series of novel 3-cyano-4-aminochromene derivatives bearing alkyl substituents at the 4-position was prepared for biological evaluation.

Results: These compounds were obtained by the addition of various Grignard reagents into Nethoxycarbonyl- 3-cyanoiminocoumarines in moderate to good yields (72-96%). The reaction is completely regioselective. The new chromene derivatives were screened for their in vitro antimicrobial activities against a panel of six bacterial and three fungal strains using agar dilution method.

Conclusion: The antibacterial activity of the chromene derivatives was more pronounced on Gram-positive bacteria than on Gram-negative bacteria with a significant activity observed against Staphylococcus aureus. An interesting antifungal activity against Fusarium sp. and Fusarium oxysporum was also noticed.

Keywords:

Antibacterial activity, Antifungal activity, Carbamates, Chromenes, Coumarins, Grignard reagents.

Affiliation:

Laboratoire de Chimie Appliquee: Heterocycles, Corps Gras et Polymères, Faculty of Science of Sfax, University of Sfax, BP1171, Sfax, Laboratory of Plant Biotechnology Applied to Crop Improvement, Faculty of Science of Sfax, University of Sfax, BP1171, Sfax, Le Mans Universite (Universite du Maine), CNRS UMR 6283, Institut des Molécules et Materiaux du Mans (IMMM), 72085 Le Mans Cedex 09, Le Mans Universite (Universite du Maine), CNRS UMR 6283, Institut des Molécules et Materiaux du Mans (IMMM), 72085 Le Mans Cedex 09, Laboratory of Plant Biotechnology Applied to Crop Improvement, Faculty of Science of Sfax, University of Sfax, BP1171, Sfax, Laboratory of Plant Biotechnology Applied to Crop Improvement, Faculty of Science of Sfax, University of Sfax, BP1171, Sfax, Le Mans Universite (Universite du Maine), CNRS UMR 6283, Institut des Molécules et Materiaux du Mans (IMMM), 72085 Le Mans Cedex 09, Laboratoire de Chimie Appliquee: Heterocycles, Corps Gras et Polymères, Faculty of Science of Sfax, University of Sfax, BP1171, Sfax



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