Divergent Synthesis of Novel 3(5)-Aminoazole-Benzopyrone Hybrids and their Evaluation as α-Glucosidase Inhibitors.

Autor: Myshko AS; V P Kukhar IBOPC of the NAS of Ukraine, Department of Chemistry of Bioactive Nitrogen-Containing Heterocyclic Bases, Academika Kukharya Str. 1, 02094, Kyiv, UKRAINE., Mrug GP; V P Kukhar IBOPC of the NAS of Ukraine, Department of Chemistry of Bioactive Nitrogen-Containing Heterocyclic Bases, Kyiv, UKRAINE., Bondarenko SP; National University of Food Technologies, Department of Food Chemistr, Kyiv, UKRAINE., Demydchuk BA; V P Kukhar IBOPC of the NAS of Ukraine, Department of Chemistry of Bioactive Nitrogen-Containing Heterocyclic Bases, Kyiv, UKRAINE., Kobzar OL; V P Kukhar IBOPC of the NAS of Ukraine, Department of Bioorganic Mechanisms, UKRAINE., Buldenko VM; V P Kukhar IBOPC of the NAS of Ukraine, Department of Bioorganic Mechanisms, UKRAINE., Vovk AI; V P Kukhar IBOPC of the NAS of Ukraine, Department of Bioorganic Mechanisms, UKRAINE., Frasinyuk M; V P Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the National Academy of Sciences: Institut bioorganicnoi himii ta naftohimii Nacional'na akademia nauk Ukraini, Department of chemistry of bioactive nitrogen containing heterocyclic bases, 1, Akademika Kukharia, 02094, Kyiv, UKRAINE.
Jazyk: angličtina
Zdroj: ChemMedChem [ChemMedChem] 2024 Nov 19, pp. e202400525. Date of Electronic Publication: 2024 Nov 19.
DOI: 10.1002/cmdc.202400525
Abstrakt: An efficient approach has been developed for the trapping in situ generated benzopyrone-based ortho-quinone methide intermediates by 3- and 5-amino pyrazoles or isoxazoles. In cases of naturally occurring phenolic Mannich bases, hybrid compounds between the azole and flavonoid, namely, coumarin, chromone, isoflavone, and aurone were synthesized in moderate to good yields. It is remarkable that depending on 3- or 5-position of the amino group, the reaction led to the formation of C-4 or 3-NH substituted azole derivatives, respectively. In vitro studies showed that some of the obtained compounds bearing 5-aminoisoxazole part exhibit inhibitory activity towards α-glucosidase with IC50 values in the micromolar range.
(© 2024 Wiley‐VCH GmbH.)
Databáze: MEDLINE
Externí odkaz: