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Ferrocene-containing tetrahydropyrazolopyrazolones: Antioxidant and antimicrobial activity
dc.creator | Bugarinović, Jovana P. | |
dc.creator | Pešić, Marko S. | |
dc.creator | Minić, Aleksandra | |
dc.creator | Katanić, Jelena | |
dc.creator | Ilić-Komatina, Danijela | |
dc.creator | Pejović, Anka | |
dc.creator | Mihailović, Vladimir B. | |
dc.creator | Stevanović, Dragana D. | |
dc.creator | Nastasijević, Branislav J. | |
dc.creator | Damljanović, Ivan S. | |
dc.date.accessioned | 2018-10-25T12:35:34Z | |
dc.date.available | 2018-10-25T12:35:34Z | |
dc.date.issued | 2018 | |
dc.identifier.issn | 0162-0134 | |
dc.identifier.issn | 1873-3344 | |
dc.identifier.uri | https://linkinghub.elsevier.com/retrieve/pii/S0162013418302472 | |
dc.identifier.uri | https://vinar.vin.bg.ac.rs/handle/123456789/7890 | |
dc.description.abstract | A 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. | en |
dc.relation | info:eu-repo/grantAgreement/MESTD/Integrated and Interdisciplinary Research (IIR or III)/43004/RS// | |
dc.relation | info:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172034/RS// | |
dc.rights | restrictedAccess | |
dc.source | Journal of Inorganic Biochemistry | |
dc.subject | Ferrocenes | en |
dc.subject | Pyrazolones | en |
dc.subject | Antioxidant activity | en |
dc.subject | Antibacterial activity | en |
dc.subject | Antifungal activity | en |
dc.subject | Cyclic voltammetry | en |
dc.title | Ferrocene-containing tetrahydropyrazolopyrazolones: Antioxidant and antimicrobial activity | en |
dc.type | article | en |
dc.rights.license | ARR | |
dcterms.abstract | Бугариновић, 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.volume | 189 | |
dc.citation.spage | 134 | |
dc.citation.epage | 142 | |
dc.identifier.wos | 000449036800014 | |
dc.identifier.doi | 10.1016/j.jinorgbio.2018.09.015 | |
dc.citation.rank | M21 | |
dc.identifier.pmid | 30265996 | |
dc.type.version | publishedVersion | |
dc.identifier.scopus | 2-s2.0-85053811669 |
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