2026-05-08T04:28:11Z https://www.eurjchem.com/index.php/eurjchem/oai

oai:ojs.www.eurjchem.com:article/1137 2015-03-31T07:18:02Z eurjchem:ART driver

Novel antimicrobial and anti-acetylcholinesterase dihydroisoxazoles from (R)-limonene Bnina, Enis Ben Romdhane, Anis Daami-Remadi, Majda Jannet, Hichem Ben Lactam (R)-Limonene Antimicrobial Cycloaddition Dihydroisoxazoles Anti-acetylcholinesterase 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). Atlanta Publishing House LLC 2015-03-31 info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion application/pdf https://www.eurjchem.com/index.php/eurjchem/article/view/1137 10.5155/eurjchem.6.1.21-30.1137 European Journal of Chemistry; Vol. 6 No. 1 (2015): March 2015; 21-30 2153-2257 2153-2249 eng https://www.eurjchem.com/index.php/eurjchem/article/view/1137/pdf_1137