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dc.creatorSimijonović, Dušica
dc.creatorPetrović, Zorica D.
dc.creatorMilovanović, Vesna M.
dc.creatorPetrović, Vladimir P.
dc.creatorBogdanović, Goran A.
dc.date.accessioned2018-06-28T07:43:40Z
dc.date.available2018-06-28T07:43:40Z
dc.date.issued2018
dc.identifier.issn2046-2069 (print)
dc.identifier.urihttp://xlink.rsc.org/?DOI=C8RA02702A
dc.identifier.urihttp://vinar.vin.bg.ac.rs/handle/123456789/7682
dc.description.abstractPyrazolyl-phthalazine-dione derivatives (PPDs) were synthetized in the ionic liquid catalyzed one-pot multicomponent reaction of acetylacetone, 2,3-dihydrophthalazine-1,4-dione, and different aldehydes in moderate to good yields. Six new PPDs were obtained, and the crystal structure of 2-acetyl-1-(4-fluorophenyl)- 3-methyl-1H-pyrazolo[1,2-b] phthalazine-5,10-dione (PPD-4) was determined. The most interesting structural features of the novel PPD-4 is the formation of a rather short intermolecular distance between the F atom of one molecule and the midpoint of the neighbouring six-membered heterocyclic ring. This interaction arranges all molecules into parallel supramolecular chains. UV-Vis spectra of all PPDs were acquired and compared to the simulated ones obtained with TD-DFT. All synthetized compounds were subjected to evaluation of their in vitro antioxidative activity using a stable DPPH radical. It was shown that PPD-7, with a catechol motive, is the most active antioxidant, while PPD-9, with two neighbouring methoxy groups to the phenolic OH, exerted a somewhat lower, but significant antioxidative potential. The results of DFT thermodynamical study are in agreement with experimental findings that PPD-7 and PPD-9 should be considered as powerful radical scavengers. In addition, the obtained theoretical results (bond dissociation and proton abstraction energies) specify SPLET as a prevailing radical scavenging mechanism in polar solvents, and HAT in solvents with lower polarity. On the other hand, the obtained reaction enthalpies for inactivation of free radicals suggest competition between HAT and SPLET mechanisms, except in the case of the (OH)-O-center dot radical in polar solvents, where HAT is labeled as prefered.en
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172016/RS//
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172014/RS//
dc.rightsopenAccess
dc.sourceRSC Advances
dc.subjectacetoneen
dc.subjectantioxidantsen
dc.subjectcrystal atomic structureen
dc.subjectfree radicalsen
dc.subjectsolventsen
dc.subjectanti-oxidative activityen
dc.subjectantiradical activitiesen
dc.titleA new efficient domino approach for the synthesis of pyrazolyl-phthalazine-diones. Antiradical activity of novel phenolic productsen
dc.typearticleen
dc.rights.licenseBY-NC
dcterms.abstractБогдановић, Горан A.; Петровић, Владимир П.; Петровић, Зорица Д.; Миловановић, Весна М.; Симијоновић, Душица;
dc.citation.volume8
dc.citation.issue30
dc.citation.spage16663
dc.citation.epage16673
dc.identifier.wos000431814500029
dc.identifier.doi10.1039/C8RA02702A
dc.type.versionpublishedVersion
dc.identifier.scopus2-s2.0-85046886740
dc.identifier.fulltexthttp://vinar.vin.bg.ac.rs//bitstream/id/10072/Simijonovic_2018_A_new_efficient_domino_approach.pdf


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