Ultrasound promoted synthesis of 2-imidazolines in water: A greener approach toward monoamine oxidase inhibitors

A series of sixteen 2-imidazolines ( 3) has been synthesized from the reaction of 1 and 2 by ultrasound irradiation with NBS in an aqueous medium in high yields (80–99%). The compound 3 ability to inhibit the activity of the A and B isoforms of monoamine oxidase (MAO) was investigated. A series of s...

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Veröffentlicht in:Bioorganic & medicinal chemistry letters 2009-01, Vol.19 (2), p.546-549
Hauptverfasser: Sant’ Anna, Gabriela da S., Machado, Pablo, Sauzem, Patricia D., Rosa, Fernanda A., Rubin, Maribel A., Ferreira, Juliano, Bonacorso, Helio G., Zanatta, Nilo, Martins, Marcos A.P.
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Sprache:eng
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Zusammenfassung:A series of sixteen 2-imidazolines ( 3) has been synthesized from the reaction of 1 and 2 by ultrasound irradiation with NBS in an aqueous medium in high yields (80–99%). The compound 3 ability to inhibit the activity of the A and B isoforms of monoamine oxidase (MAO) was investigated. A series of sixteen 2-substituted-2-imidazolines (where the substituent R = Ph, Me-4-Ph; MeO-4-Ph; (MeO) 2-3,4-Ph; (MeO) 3-3,4,5-Ph; Ph-4-O-C(O)-Ph; Cl-4-Ph; Cl-2-Ph; Cl 2-2,4-Ph; NO 2-4-Ph; NO 2-3-Ph; Naphth-2-yl; Fur-2-yl; Benzofur-2-yl; Pyridin-2-yl; Quinolin-2-yl) has been synthesized from the reaction of the substituted-aldehydes and ethylenediamine by ultrasound irradiation with NBS in an aqueous medium in high yields (80–99%). The 2-imidazoline ability to inhibit the activity of the A and B isoforms of monoamine oxidase (MAO) was investigated and some of them showed potent and selective MAO inhibitory activity especially for the MAO-B isoform and could become promising candidates for future development.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2008.03.001