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dc.creatorBugarinović, Jovana P.
dc.creatorPešić, Marko S.
dc.creatorMinić, Aleksandra
dc.creatorKatanić, Jelena
dc.creatorIlić-Komatina, D
dc.creatorPejović, Anka
dc.creatorMihailović, Vladimir B.
dc.creatorStevanović, Dragana D.
dc.creatorNastasijević, Branislav J.
dc.creatorDamljanović, Ivan S.
dc.date.accessioned2018-10-25T12:35:34Z
dc.date.available2018-10-25T12:35:34Z
dc.date.issued2018
dc.identifier.issn0162-0134 (print)
dc.identifier.issn1873-3344 (electronic)
dc.identifier.urihttps://linkinghub.elsevier.com/retrieve/pii/S0162013418302472
dc.identifier.urihttp://vinar.vin.bg.ac.rs/handle/123456789/7890
dc.description.abstractA series of ferrocenes which contain dinitrogen-fused pyrazolidinone ring were synthesized from acryloylferrocene (4) and N,N′‑cyclic azomethine imines (3). Novel 5‑aryl‑6‑ferrocenoyltetrahydropyrazolo[1,2‑a]pyrazol‑1(5H)-ones were obtained as mixtures of two diastereoisomers (trans and cis) which were separated and isolated as pure substances. Ortho-substituted N,N′‑cyclic azomethine imines 5-oxo-2-(2,4,6-trimethylbenzylidene)pyrazolidin-2-ium-1-ide (3e) and 2-(2-methoxybenzylidene)-5-oxopyrazolidin-2-ium-1-ide (3f) reacted stereoselectively affording only trans-6-ferrocenoyl-5-mesityltetrahydropyrazolo[1,2-a]pyrazol-1(5H)-one (5e) and 6-ferrocenoyl-5-(2-methoxyphenyl)tetrahydropyrazolo[1,2-a]pyrazol-1(5H)-one (5f). Ferrocenyl derivatives were screened for in vitro antioxidant and antifungal activities and excellent DPPH and ABTS radicals scavenging activity was observed with majority of tested 5‑aryl‑6‑ferrocenoyltetrahydropyrazolo[1,2‑a]pyrazol‑1(5H)-ones. Several tested compounds showed selective scavenging properties neutralizing ABTS•+ radical cations in contrast to inactivity toward DPPH[rad] radicals. Trans-5-aryl-6-ferrocenoyltetrahydropyrazolo[1,2-a]pyrazol-1(5H)-ones 5b, 5c, 5d, 5j as well as cis-6-ferrocenoyl-5-(p-tolyl)tetrahydropyrazolo[1,2-a]pyrazol-1(5H)-one (6d) displayed fungal growth inhibition at low concentration against C. albicans and/or A. brasiliensis. Molecular docking studies revealed that the cis-6-ferrocenoyl-5-(4-nitrophenyl)tetrahydropyrazolo[1,2-a]pyrazol-1(5H)-one (6l) and cis-6-ferrocenoyl-5-(naphthalen-2-yl)tetrahydropyrazolo[1,2-a]pyrazol-1(5H)-one (6n) have potential to become lead molecules in drug discovery process. © 2018 Elsevier Inc.
dc.relationinfo:eu-repo/grantAgreement/MESTD/Integrated and Interdisciplinary Research (IIR or III)/43004/RS//
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172034/RS//
dc.rightsrestrictedAccess
dc.sourceJournal of Inorganic Biochemistry
dc.subjectFerrocenesen
dc.subjectPyrazolonesen
dc.subjectAntioxidant activityen
dc.subjectAntibacterial activityen
dc.subjectAntifungal activityen
dc.subjectCyclic voltammetryen
dc.titleFerrocene-containing tetrahydropyrazolopyrazolones: Antioxidant and antimicrobial activityen
dc.typearticleen
dc.rights.licenseARR
dcterms.abstractБугариновић, Ј.П.; Пешић, М.С.; Минић, A; Катанић, Ј; Илић-Коматина, Д; Пејовић, A; Михаиловић, В; Стевановић, Д; Настасијевић, Б; Дамљановић, И;
dc.rights.holder© 2018 Elsevier Inc
dc.citation.volume189
dc.citation.spage134
dc.citation.epage142
dc.identifier.wos000449036800014
dc.identifier.doi10.1016/j.jinorgbio.2018.09.015
dc.identifier.pmid30265996
dc.type.versionpublishedVersion
dc.identifier.scopus2-s2.0-85053811669


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