European Journal of Chemistry 2015, 6(1), 21-30. doi:10.5155/eurjchem.6.1.21-30.1137

Novel antimicrobial and anti-acetylcholinesterase dihydroisoxazoles from (R)-limonene


Enis Ben Bnina (1) , Anis Romdhane (2) , Majda Daami-Remadi (3) , Hichem Ben Jannet (4,*)

(1) Laboratoire de Chimie Hétérocyclique, Produits Naturels et Réactivité, Equipe: Chimie Médicinale et Produits Naturels, Faculté des Sciences de Monastir, Université de Monastir, Avenue de l’Environnement, 5019 Monastir, Tunisie
(2) Laboratoire de Chimie Hétérocyclique, Produits Naturels et Réactivité, Equipe: Chimie Médicinale et Produits Naturels, Faculté des Sciences de Monastir, Université de Monastir, Avenue de l’Environnement, 5019 Monastir, Tunisie
(3) UR13AGR09, Production Horticole Intégrée au Centre Est Tunisien, Centre Régional des Recherches en Horticulture et Agriculture Biologique de Chott-Mariem, Université de Sousse, 4042, Chott-Mariem, Tunisie
(4) Laboratoire de Chimie Hétérocyclique, Produits Naturels et Réactivité, Equipe: Chimie Médicinale et Produits Naturels, Faculté des Sciences de Monastir, Université de Monastir, Avenue de l’Environnement, 5019 Monastir, Tunisie
(*) Corresponding Author

Received: 22 Aug 2014, Accepted: 19 Sep 2014, Published: 31 Mar 2015

Abstract


We report herein the convenient procedures for the efficient and easy synthesis, and the antimicrobial and the anti-acetylcholinesterase evaluation of two new series of (R)-limonene derivatives. A substantial modification aimed at targeting to discover novel structures with a better antimicrobial and anti-acetylcholinesterase (anti-AChE) activities. The condensation of (R)-limonene (1) with various arylnitrile oxides led, via the 1,3-dipolar cycloaddition reaction, conducted with complete region-specificity, to a series of new limonene-dihydroisoxazoles, 2a-h. On the other hand, N-alkylation of the previously prepared limonene-lactam derivative (3) yielded the corresponding dipolarophile (4), which affords by condensation with arylnitrile oxides the expected new dihydroisoxazoles, 5a-h. The target compounds were completely characterized by 1H NMR, 13C NMR and MS. All the synthesized heterocyclic compounds were tested for their antimicrobial and anti-acetylcholinesterase activities. The dihydroisoxazoles 2a (IZ = 13.25 mm, cc = 1 mg/mL) and 5b (IZ = 13.75 mm, cc = 1 mg/mL) exhibited the highest antifungal activity. The greatest anti-acetylcolinesterase activity was exhibited by 2f (IC50 = 82±3 µg/mL) and by 5a (IC50 = 99±1 µg/mL).


Keywords


Lactam; (R)-Limonene; Antimicrobial; Cycloaddition; Dihydroisoxazoles; Anti-acetylcholinesterase

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DOI: 10.5155/eurjchem.6.1.21-30.1137

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How to cite


Bnina, E.; Romdhane, A.; Daami-Remadi, M.; Jannet, H. Eur. J. Chem. 2015, 6(1), 21-30. doi:10.5155/eurjchem.6.1.21-30.1137
Bnina, E.; Romdhane, A.; Daami-Remadi, M.; Jannet, H. Novel antimicrobial and anti-acetylcholinesterase dihydroisoxazoles from (R)-limonene. Eur. J. Chem. 2015, 6(1), 21-30. doi:10.5155/eurjchem.6.1.21-30.1137
Bnina, E., Romdhane, A., Daami-Remadi, M., & Jannet, H. (2015). Novel antimicrobial and anti-acetylcholinesterase dihydroisoxazoles from (R)-limonene. European Journal of Chemistry, 6(1), 21-30. doi:10.5155/eurjchem.6.1.21-30.1137
Bnina, Enis, Anis Romdhane, Majda Daami-Remadi, & Hichem Ben Jannet. "Novel antimicrobial and anti-acetylcholinesterase dihydroisoxazoles from (R)-limonene." European Journal of Chemistry [Online], 6.1 (2015): 21-30. Web. 23 Oct. 2019
Bnina, Enis, Romdhane, Anis, Daami-Remadi, Majda, AND Jannet, Hichem. "Novel antimicrobial and anti-acetylcholinesterase dihydroisoxazoles from (R)-limonene" European Journal of Chemistry [Online], Volume 6 Number 1 (31 March 2015)

DOI Link: https://doi.org/10.5155/eurjchem.6.1.21-30.1137

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