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Green synthesis of bis-(β-dicarbonyl)-methane derivatives and biological evaluation as putative anticandidial agents
dc.creator | Tzani, Andromachi | |
dc.creator | Vaitsis, Christos | |
dc.creator | Kritsi, Eftichia | |
dc.creator | Ivanov, Marija | |
dc.creator | Soković, Marina | |
dc.creator | Zoumpoulakis, Panagiotis | |
dc.creator | Detsi, Anastasia | |
dc.date.accessioned | 2020-05-08T10:43:18Z | |
dc.date.available | 2900-01-01 | |
dc.date.issued | 2020 | |
dc.identifier.issn | 0022-2860 | |
dc.identifier.uri | https://radar.ibiss.bg.ac.rs/handle/123456789/3662 | |
dc.description.abstract | In this work the effectiveness of two different reaction media, an Ionic Liquid (IL) and a Deep Eutectic Solvent (DES), as greener, alternative solvents for the synthesis of bioactive bis-(β-dicarbonyl)-methane derivatives is examined. A domino Knoevenagel-Michael reaction between selected aromatic aldehydes and heterocyclic 1,3-dicarbonyl compounds was successfully accomplished, producing the desired compounds in satisfactory yields. The solvents were recycled and reused three times without noticeable decrease in reaction yields. A putative conformation of compound 4g was determined using NMR spectroscopy and an “anti” orientation of the fused aromatic rings was proposed. Moreover, some of the bis-(β-dicarbonyl)-methane derivatives were tested for their antifungal activity against four Candida albicans strains. Biscoumarin 6 and bisquinolinone 4d exhibited promising anticandidial activity. In parallel, in silico ligand-based similarity calculations provided a putative mechanism of action of the examined compounds through CYP51 inhibition. | en |
dc.publisher | Elsevier B.V. | |
dc.relation | info:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/173032/RS/ | |
dc.relation | National Technical University of Athens | |
dc.rights | restrictedAccess | |
dc.source | Journal of Molecular Structure | |
dc.subject | Antifungal activity | |
dc.subject | Bis-(β-dicarbonyl)-methane derivatives | |
dc.subject | Deep eutectic solvent | |
dc.subject | Ionic liquid | |
dc.title | Green synthesis of bis-(β-dicarbonyl)-methane derivatives and biological evaluation as putative anticandidial agents | en |
dc.type | article | en |
dc.rights.license | ARR | |
dcterms.abstract | Критси, Ефтицхиа; Зоумпоулакис, Панагиотис; Ваитсис, Цхристос; Тзани, Aндромацхи; Детси, Aнастасиа; Соковић, Марина; Смиљковић, Марија; | |
dc.rights.holder | © 2020 Elsevier B.V. | |
dc.citation.volume | 1216 | |
dc.identifier.doi | 10.1016/j.molstruc.2020.128276 | |
dc.identifier.scopus | 2-s2.0-85083757778 | |
dc.identifier.wos | 000545897700015 | |
dc.citation.apa | Tzani, A., Vaitsis, C., Kritsi, E., Smiljkovic, M., Sokovic, M., Zoumpoulakis, P., et al. (2020). Green synthesis of bis-(β-dicarbonyl)-methane derivatives and biological evaluation as putative anticandidial agents. Journal of Molecular Structure, 1216, 128276. | |
dc.citation.vancouver | Tzani A, Vaitsis C, Kritsi E, Smiljkovic M, Sokovic M, Zoumpoulakis P, Detsi A. Green synthesis of bis-(β-dicarbonyl)-methane derivatives and biological evaluation as putative anticandidial agents. J Mol Struct. 2020;1216:128276. | |
dc.citation.spage | 128276 | |
dc.type.version | publishedVersion | |
dc.citation.rank | M23 |