{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T03:22:01Z","timestamp":1760239321529,"version":"build-2065373602"},"reference-count":54,"publisher":"MDPI AG","issue":"21","license":[{"start":{"date-parts":[[2020,10,26]],"date-time":"2020-10-26T00:00:00Z","timestamp":1603670400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100008742","name":"Camilo Jos\u00e9 Cela University","doi-asserted-by":"publisher","award":["UCJC-2018-04"],"award-info":[{"award-number":["UCJC-2018-04"]}],"id":[{"id":"10.13039\/501100008742","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>Herein we report the synthesis, antioxidant and neuroprotective power of homo-tris-nitrones (HTN) 1-3, designed on the hypothesis that the incorporation of a third nitrone motif into our previously identified homo-bis-nitrone 6 (HBN6) would result in an improved and stronger neuroprotection. The neuroprotection of HTNs 1-3, measured against oligomycin A\/rotenone, showed that HTN2 was the best neuroprotective agent at a lower dose (EC50 = 51.63 \u00b1 4.32 \u03bcM), being similar in EC50 and maximal activity to \u03b1-phenyl-N-tert-butylnitrone (PBN) and less potent than any of HBNs 4-6. The results of neuroprotection in an in vitro oxygen glucose deprivation model showed that HTN2 was the most powerful (EC50 = 87.57 \u00b1 3.87 \u03bcM), at lower dose, but 50-fold higher than its analogous HBN5, and \u22481.7-fold less potent than PBN. HTN3 had a very good antinecrotic (IC50 = 3.47 \u00b1 0.57 \u03bcM), antiapoptotic, and antioxidant (EC50 = 6.77 \u00b1 1.35 \u03bcM) profile, very similar to that of its analogous HBN6. In spite of these results, and still being attractive neuroprotective agents, HTNs 2 and 3 do not have better neuroprotective properties than HBN6, but clearly exceed that of PBN.<\/jats:p>","DOI":"10.3390\/ijms21217949","type":"journal-article","created":{"date-parts":[[2020,10,27]],"date-time":"2020-10-27T09:22:45Z","timestamp":1603790565000},"page":"7949","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Homo-Tris-Nitrones Derived from \u03b1-Phenyl-N-tert-butylnitrone: Synthesis, Neuroprotection and Antioxidant Properties"],"prefix":"10.3390","volume":"21","author":[{"given":"Daniel","family":"Diez-Iriepa","sequence":"first","affiliation":[{"name":"Laboratory of Medicinal Chemistry, Institute of Organic Chemistry (CSIC), Juan de la Cierva 3, 28006 Madrid, Spain"},{"name":"Department of Organic Chemistry and Inorganic Chemistry, Alcal\u00e1 University, Alcal\u00e1 de Henares, 28805 Madrid, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Beatriz","family":"Chamorro","sequence":"additional","affiliation":[{"name":"Department of Biochemistry and Molecular Biology, Faculty of Pharmacy, Complutense University of Madrid, Plaza Ram\u00f3n y Cajal s\/n, Ciudad Universitaria, 28040 Madrid, Spain"},{"name":"Faculty of Health, Camilo Jos\u00e9 Cela University of Madrid (UCJC), 28692 Villafranca del Castillo, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Marta","family":"Talav\u00e1n","sequence":"additional","affiliation":[{"name":"Department of Biochemistry and Molecular Biology, Faculty of Pharmacy, Complutense University of Madrid, Plaza Ram\u00f3n y Cajal s\/n, Ciudad Universitaria, 28040 Madrid, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mourad","family":"Chioua","sequence":"additional","affiliation":[{"name":"Laboratory of Medicinal Chemistry, Institute of Organic Chemistry (CSIC), Juan de la Cierva 3, 28006 Madrid, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3475-9624","authenticated-orcid":false,"given":"Isabel","family":"Iriepa","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry and Inorganic Chemistry, Alcal\u00e1 University, Alcal\u00e1 de Henares, 28805 Madrid, Spain"},{"name":"Institute of Chemical Research Andr\u00e9s M. del R\u00edo, Alcal\u00e1 University, Alcal\u00e1 de Henares, 28805 Madrid, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1844-350X","authenticated-orcid":false,"given":"Dimitra","family":"Hadjipavlou-Litina","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry, School of Pharmacy, Faculty of Health Sciences, Aristotle University of Thessaloniki, 54124 Thessaloniki, Greece"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5188-6038","authenticated-orcid":false,"given":"Francisco","family":"L\u00f3pez-Mu\u00f1oz","sequence":"additional","affiliation":[{"name":"Faculty of Health, Camilo Jos\u00e9 Cela University of Madrid (UCJC), 28692 Villafranca del Castillo, Spain"},{"name":"Neuropsychopharmacology Unit, \u201cHospital 12 de Octubre\u201d Research Institute, 28041 Madrid, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jos\u00e9","family":"Marco-Contelles","sequence":"additional","affiliation":[{"name":"Laboratory of Medicinal Chemistry, Institute of Organic Chemistry (CSIC), Juan de la Cierva 3, 28006 Madrid, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7223-0222","authenticated-orcid":false,"given":"Mar\u00eda Jes\u00fas","family":"Oset-Gasque","sequence":"additional","affiliation":[{"name":"Department of Biochemistry and Molecular Biology, Faculty of Pharmacy, Complutense University of Madrid, Plaza Ram\u00f3n y Cajal s\/n, Ciudad Universitaria, 28040 Madrid, Spain"},{"name":"Instituto Universitario de Investigaci\u00f3n en Neuroqu\u00edmica, Universidad Complutense de Madrid, 28040 Madrid, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2020,10,26]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Tanaka, M., Boh\u00e1r, Z., and V\u00e9csei, L. (2020). Are kynurenines accomplices or principal villains in dementia? Maintenance of kynurenine metabolism. Molecules, 25.","DOI":"10.3390\/molecules25030564"},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Tanaka, M., and V\u00e9csei, L. (2020). Monitoring the redox status in multiple sclerosis. Biomedicines, 8.","DOI":"10.20944\/preprints202007.0737.v3"},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"Catanesi, M., d\u2019Angelo, M., Tupone, M.G., Benedetti, E., Giordano, A., Castelli, V., and Cimini, A. (2020). 438 MicroRNAs dysregulation and mitochondrial dysfunction in neurodegenerative diseases. Int. J. Mol. Sci., 21.","DOI":"10.3390\/ijms21175986"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"785","DOI":"10.1002\/biof.1388","article-title":"Antioxidants: Wonder drugs or quackery?","volume":"43","author":"Azzi","year":"2017","journal-title":"BioFactors"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"59","DOI":"10.1038\/83358","article-title":"The proteolytic activity of tissue-plasminogen activator enhances NMDA receptor-mediated signaling","volume":"7","author":"Nicole","year":"2001","journal-title":"Nat. Med."},{"key":"ref_6","doi-asserted-by":"crossref","unstructured":"Chow, C.K. (1988). Cellular Antioxidant Defense Mechanisms, CRC Press.","DOI":"10.1016\/0891-5849(89)90105-6"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"2006","DOI":"10.2174\/1568026617666170303115324","article-title":"Nitrone derivatives as therapeutics: From chemical modification to specific-targeting","volume":"17","author":"Rosselin","year":"2017","journal-title":"Curr. Top. Med. Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"1159","DOI":"10.1002\/med.21461","article-title":"NO and HNO donors, nitrones, and nitroxides: Past, present, and future","volume":"38","author":"Oliveira","year":"2018","journal-title":"Med. Res. Rev."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1361","DOI":"10.1016\/j.freeradbiomed.2008.08.017","article-title":"Nitrones as therapeutics","volume":"45","author":"Floyd","year":"2008","journal-title":"Free Radic. Biol. Med."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"309","DOI":"10.1016\/j.niox.2011.05.007","article-title":"Nitrones are able to release nitric oxide in aqueous environment under hydroxyl free radical attack","volume":"25","author":"Croitoru","year":"2011","journal-title":"Nitric Oxide"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"12498","DOI":"10.1021\/jp804929d","article-title":"Reactivity of superoxide radical anion and hydroperoxyl radical with alpha-phenyl-N-tert-butylnitrone (PBN) derivatives","volume":"112","author":"Durand","year":"2008","journal-title":"J. Phys. Chem. A"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"267","DOI":"10.1016\/0006-8993(94)91689-6","article-title":"Phenyl-tert-butyl-nitrone reduces cortical infarct and edema in rats subjected to focal ischemia","volume":"644","author":"Cao","year":"1994","journal-title":"Brain Res."},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Lapchak, P.A., and Zhang, J.H. (2017). Nitrones, Old fellows for new therapies in ischemic stroke. Neuroprotective Therapy for Stroke and Ischemic Disease, Springer. Chapter 9.","DOI":"10.1007\/978-3-319-45345-3"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1071","DOI":"10.2165\/00023210-200418150-00003","article-title":"Nitrone-related therapeutics: Potential of NXY-059 for the treatment of acute ischaemic stroke","volume":"18","author":"Maples","year":"2004","journal-title":"CNS Drugs"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"112020","DOI":"10.1016\/j.ejmech.2019.112020","article-title":"Bridging free radical chemistry with drug discovery: A promising way for finding novel drugs efficiently","volume":"189","author":"Liu","year":"2020","journal-title":"Eur. J. Med. Chem."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"145","DOI":"10.1016\/j.freeradbiomed.2013.01.033","article-title":"Nitrone-based therapeutics for neurodegenerative diseases: Their use alone or in combination with lanthionines","volume":"62","author":"Floyd","year":"2013","journal-title":"Free Rad. Biol. Med."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"931","DOI":"10.1016\/j.freeradbiomed.2011.04.014","article-title":"Translational research involving oxidative stress and diseases of aging","volume":"51","author":"Floyd","year":"2011","journal-title":"Free Radic. Biol. Med."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"32491","DOI":"10.1074\/jbc.M111.255877","article-title":"Alpha-phenyl-N-tert-butylnitrone (PBN) prevents light-induced degeneration of the retina by inhibiting RPE65 protein isomerohydrolase activity","volume":"286","author":"Mandal","year":"2011","journal-title":"J. Biol. Chem."},{"key":"ref_19","doi-asserted-by":"crossref","unstructured":"Ewert, D., Hu, N., Du, X., Li, W., West, M.B., Choi, C.-H., Floyd, R., and Kopke, R.D. (2017). HPN-07, a free radical spin trapping agent, protects against functional, cellular and electrophysiological changes in the cochlea induced by acute acoustic trauma. PLoS ONE, 12.","DOI":"10.1371\/journal.pone.0183089"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"321","DOI":"10.3109\/10715768609080971","article-title":"Phenyl-t-butyl-nitrone is active against traumatic shock in rats","volume":"1","author":"Novelli","year":"1986","journal-title":"Free Radic. Res. Commun."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"3995","DOI":"10.1016\/j.bmc.2009.04.004","article-title":"N-tert-Butyl and N-methyl nitrones derived from aromatic aldehydes inhibit macromolecular permeability increase induced by ischemia\/reperfusion in hamsters","volume":"17","author":"Dias","year":"2009","journal-title":"Bioorg. Med. Chem."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"8868","DOI":"10.1016\/j.bmc.2008.08.075","article-title":"Antioxidative and Thrombolytic TMP Nitrone for Treatment of Ischemic Stroke","volume":"16","author":"Sun","year":"2008","journal-title":"Bioorg. Med. Chem."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"1662","DOI":"10.1002\/jnr.23034","article-title":"Therapeutic effects of tetramethylpyrazine nitrone in rat ischemic stroke models","volume":"90","author":"Sun","year":"2012","journal-title":"J. Neurosci. Res."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"37148","DOI":"10.1038\/srep37148","article-title":"Tetramethylpyrazine nitrone, a multifunctional neuroprotective agent for ischemic stroke therapy","volume":"6","author":"Zhang","year":"2016","journal-title":"Sci. Rep."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"3939","DOI":"10.1016\/j.bmc.2012.04.016","article-title":"Novel multi-functional nitrones for treatment of ischemic stroke","volume":"20","author":"Sun","year":"2012","journal-title":"Bioorg. Med. Chem."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"2495","DOI":"10.1016\/j.bbamem.2017.09.026","article-title":"Cholesterol-nitrone conjugates as protective agents against lipid oxidation: A model membrane study","volume":"1859","author":"Socrier","year":"2017","journal-title":"BBA Biomembranes"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"7405","DOI":"10.1016\/j.bmcl.2010.10.037","article-title":"Cholesterol-based-phenyl-N-tert-butyl nitrone derivatives as antioxidants against light-induced retinal degeneration","volume":"20","author":"Choteau","year":"2010","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"231","DOI":"10.1016\/j.electacta.2016.02.038","article-title":"Electrochemical and spin-trapping properties of para-substituted \u03b1-phenyl-N-tert-butyl nitrones","volume":"193","author":"Rosselin","year":"2016","journal-title":"Electrochim. Acta"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"2087","DOI":"10.1039\/P29950002087","article-title":"\u03b2-Phosphorylated \u03b1-phenyl-N-tert-butylnitrone (PBN) analogues: A new series of spin traps for oxyl radicals","volume":"2","author":"Zeghdaoui","year":"1995","journal-title":"J. Chem. Soc. Perkin Trans."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"51","DOI":"10.1006\/abbi.2001.2657","article-title":"N-2-(2-Ethoxycarbonyl-propyl) \u03b1-phenylnitrone: An efficacious lipophilic spin trap for superoxide detection","volume":"397","author":"Roubaud","year":"2002","journal-title":"Arch. Biochem. Biophys."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"6615","DOI":"10.1021\/jo501121g","article-title":"Reactivities of substituted \u03b1-phenyl-N-tert -butyl nitrones","volume":"79","author":"Rosselin","year":"2014","journal-title":"J. Org. Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"6073","DOI":"10.1021\/acs.joc.0c00563","article-title":"Substituted \u03b1-phenyl and \u03b1-naphthlyl-N-tert-butyl nitrones: Synthesis, spin-trapping, and neuroprotection evaluation","volume":"85","author":"Deletraz","year":"2020","journal-title":"J. Org. Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"3012","DOI":"10.1016\/j.bmcl.2005.04.043","article-title":"Nitrone derivatives of trolox as neuroprotective agents","volume":"15","author":"Balogh","year":"2005","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"153","DOI":"10.1021\/jm201105a","article-title":"Aryl-N-alkyl nitrones, as potential agents for stroke treatment: Synthesis, theoretical calculations, antioxidant, anti-inflammatory, neuroprotective and brain-blood barrier permeability properties","volume":"55","author":"Chioua","year":"2012","journal-title":"J. Med. Chem."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"6704","DOI":"10.1021\/acs.jmedchem.5b00755","article-title":"Cholesteronitrones for stroke","volume":"58","author":"Ayuso","year":"2015","journal-title":"J. Med. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"2202","DOI":"10.1021\/acschemneuro.7b00126","article-title":"Quinolinylnitrone RP19 induces neuroprotection after transient brain ischemia","volume":"8","author":"Ayuso","year":"2017","journal-title":"ACS Chem. Neurosci."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"2703","DOI":"10.1021\/acschemneuro.9b00152","article-title":"Novel quinolylnitrones combining neuroprotective and antioxidant properties","volume":"10","author":"Chioua","year":"2019","journal-title":"ACS Chem. Neurosci."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"2184","DOI":"10.1021\/acs.jmedchem.8b01987","article-title":"New quinolylnitrones for stroke therapy: Antioxidant and neuroprotective (Z)-N-tert-butyl-1-(2-chloro-6-methoxyquinolin-3-yl)methanimine oxide as a new lead-compound for ischemic stroke treatment","volume":"62","author":"Chioua","year":"2019","journal-title":"J. Med. Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"4678","DOI":"10.1021\/ja011507s","article-title":"Stilbazulenyl nitrone (STAZN): A nitronyl-substituted hydrocarbon with the potency of classical phenolic chain-breaking antioxidants","volume":"124","author":"Becker","year":"2002","journal-title":"J. Am. Chem. Soc."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"330","DOI":"10.1002\/ana.10659","article-title":"Stilbazulenyl nitrone, a novel antioxidant, is highly neuroprotective in focal ischemia","volume":"54","author":"Ginsberg","year":"2003","journal-title":"Ann. Neurol."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"209","DOI":"10.1007\/s12975-011-0071-7","article-title":"De-risking of stilbazulenyl nitrone (stazn), a lipophilic nitrone to treat stroke using a unique panel of in vitro assays","volume":"2","author":"Lapchak","year":"2011","journal-title":"Trans. Stroke Res."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"738","DOI":"10.1016\/S0891-5849(97)00338-9","article-title":"Azulenyl nitrones: Colorimetric detection of oxyradical end products and neuroprotection in the gerbil transient forebrain ischemia\/reperfusion model","volume":"24","author":"Althaus","year":"1998","journal-title":"Free Radical Biol. Med."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"245","DOI":"10.1007\/s11481-013-9514-0","article-title":"The novel tetramethypyrazine bis-nitrone (TN-2) protects against MPTP\/MPP+-induced neurotoxicity via inhibition of mitochondrial-dependent apoptosis","volume":"9","author":"Xu","year":"2014","journal-title":"J. Neuroimmune Pharmacol."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"76","DOI":"10.1016\/j.neuint.2014.09.001","article-title":"A Novel Tetramethylpyrazine bis-nitrone (TN-2) protects against 6-hydroxyldopamine-induced neurotoxicity via modulation of the NF-\u03baB and the PKC\u03b1\/PI3-K\/Akt pathways","volume":"78","author":"Xu","year":"2014","journal-title":"Neurochem. Int."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"770","DOI":"10.2174\/1570180811666140121234608","article-title":"Pharmacokinetic analysis of tetramethylpyrazine bis-nitrone TN-2 in rats and its protein binding in vitro","volume":"11","author":"Sun","year":"2014","journal-title":"Lett. Drug Des. Discov."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"14150","DOI":"10.1038\/s41598-020-70690-y","article-title":"Synthesis, antioxidant properties and neuroprotection of \u03b1-phenyl-tert-butylnitrone derived HomoBisNitrones in in vitro and in vivo ischemia models","volume":"10","author":"Chamorro","year":"2020","journal-title":"Sci. Rep."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"1675","DOI":"10.1016\/S0379-6779(97)80393-1","article-title":"Synthesis and magnetic properties of stable nitroxyl tri-radicals","volume":"85","author":"Tien","year":"1997","journal-title":"Synth. Metals"},{"key":"ref_48","first-page":"S22","article-title":"Spin trapping agents for the treatment of diseases associated with oxidation of lipids and proteins","volume":"32","author":"Carney","year":"1992","journal-title":"PCT Int. Appl."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"445","DOI":"10.1016\/j.bioorg.2019.01.071","article-title":"Synthesis, neuroprotective and antioxidant capacity of PBN-related indanonitrones","volume":"86","author":"Chioua","year":"2019","journal-title":"Bioorg. Chem."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"178","DOI":"10.1016\/j.ejmech.2016.04.023","article-title":"Potent anticholinesterasic and neuroprotective pyranotacrines as inhibitors of beta-amyloid aggregation, oxidative stress and tau-phosphorylation for Alzheimer\u2019s disease","volume":"118","author":"Hayour","year":"2016","journal-title":"Eur. J. Med. Chem."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"78","DOI":"10.1002\/jnr.20853","article-title":"Nitric oxide andperoxynitrite induce cellular death in bovine chromaffin cells: Evidence for a mixed necrotic and apoptotic mechanism with caspases activation","volume":"84","author":"Vicente","year":"2006","journal-title":"J. Neurosci. Res."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"8581","DOI":"10.1021\/acsomega.9b00189","article-title":"Synthesis and neuroprotective properties of N-substituted C-dialkoxyphosphorylated nitrones","volume":"16","author":"Piotrowska","year":"2019","journal-title":"ACS Omega"},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"9655","DOI":"10.3390\/molecules19079655","article-title":"Novel cinnamic acid derivatives as antioxidant and anticancer agents: Design, synthesis and modeling studies","volume":"19","author":"Pontiki","year":"2014","journal-title":"Molecules"},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"8334","DOI":"10.1002\/slct.201901271","article-title":"Synthesis, monoamine oxidase inhibition and computational analysis of diversely substituted N-propargylated-1,3,5-triazines","volume":"4","author":"Chioua","year":"2019","journal-title":"ChemistrySelect"}],"container-title":["International Journal of Molecular Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1422-0067\/21\/21\/7949\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T10:28:35Z","timestamp":1760178515000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1422-0067\/21\/21\/7949"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,10,26]]},"references-count":54,"journal-issue":{"issue":"21","published-online":{"date-parts":[[2020,11]]}},"alternative-id":["ijms21217949"],"URL":"https:\/\/doi.org\/10.3390\/ijms21217949","relation":{},"ISSN":["1422-0067"],"issn-type":[{"type":"electronic","value":"1422-0067"}],"subject":[],"published":{"date-parts":[[2020,10,26]]}}}