{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,31]],"date-time":"2026-08-31T21:40:15Z","timestamp":1788212415580,"version":"build-2803163510"},"reference-count":59,"publisher":"MDPI AG","issue":"6","license":[{"start":{"date-parts":[[2025,3,17]],"date-time":"2025-03-17T00:00:00Z","timestamp":1742169600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"\u201cIuliu Ha\u021bieganu\u201d University of Medicine and Pharmacy, Cluj-Napoca, Romania","award":["771\/17\/11.01.2023"],"award-info":[{"award-number":["771\/17\/11.01.2023"]}]},{"name":"\u201cIuliu Ha\u021bieganu\u201d University of Medicine and Pharmacy, Cluj-Napoca, Romania","award":["647\/17\/11.01.2024"],"award-info":[{"award-number":["647\/17\/11.01.2024"]}]},{"name":"\u201cIuliu Ha\u021bieganu\u201d University of Medicine and Pharmacy, Cluj-Napoca, Romania","award":["27N\/03.01.2023"],"award-info":[{"award-number":["27N\/03.01.2023"]}]},{"name":"National Research Development and Innovation Plan 2022\u20132027, Romania","award":["771\/17\/11.01.2023"],"award-info":[{"award-number":["771\/17\/11.01.2023"]}]},{"name":"National Research Development and Innovation Plan 2022\u20132027, Romania","award":["647\/17\/11.01.2024"],"award-info":[{"award-number":["647\/17\/11.01.2024"]}]},{"name":"National Research Development and Innovation Plan 2022\u20132027, Romania","award":["27N\/03.01.2023"],"award-info":[{"award-number":["27N\/03.01.2023"]}]},{"name":"Installations and Special Objectives of National Interest (IOSIN), IZOSTAB","award":["771\/17\/11.01.2023"],"award-info":[{"award-number":["771\/17\/11.01.2023"]}]},{"name":"Installations and Special Objectives of National Interest (IOSIN), IZOSTAB","award":["647\/17\/11.01.2024"],"award-info":[{"award-number":["647\/17\/11.01.2024"]}]},{"name":"Installations and Special Objectives of National Interest (IOSIN), IZOSTAB","award":["27N\/03.01.2023"],"award-info":[{"award-number":["27N\/03.01.2023"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Reactive oxygen species play a significant role in various pathological conditions, driving the need for novel, potent antioxidants. While polyphenols are known for their antioxidant properties, their limited stability and bioavailability present challenges for therapeutic applications. To address these limitations, a series of novel thiazolyl-polyphenolic compounds was synthesized via a multi-step synthetic route incorporating Hantzsch heterocyclization in the final step. The synthesized compounds 7a\u2013k were structurally characterized using spectroscopic techniques, including NMR, MS, and IR. In silico thermodynamic calculations, including HOMO\u2013LUMO gap and bond dissociation enthalpy (BDE) calculations, revealed a promising antioxidant profile for these compounds and indicated that the substitution in position 2 of the thiazole ring does not substantially influence the antioxidant activity conferred by the catechol moiety in position 4. The antioxidant capacity of the synthesized compounds was experimentally validated using a panel of six distinct assays: two radical scavenging assays (ABTS and DPPH) and four electron transfer-based assays (RP, TAC, FRAP, and CUPRAC). The in vitro evaluation demonstrated that compounds 7j and 7k exhibited significantly enhanced antioxidant activity compared to the established antioxidant standards, ascorbic acid and Trolox. These findings suggest that the strategic modifications in position 2 of the thiazole scaffold represent a promising direction for future research aimed at developing novel therapeutic agents with enhanced antioxidant properties. The present study is limited to the in vitro evaluation of compounds based on the N-methyl substituted thiazole scaffold, but future studies can include modifications such as changing the substituent on the thiazole nitrogen, the hydrazone linker or possible insertion of substituents in position 5 of thiazole ring of substituents with various electronic or physico-chemical properties.<\/jats:p>","DOI":"10.3390\/molecules30061345","type":"journal-article","created":{"date-parts":[[2025,3,17]],"date-time":"2025-03-17T15:24:56Z","timestamp":1742225096000},"page":"1345","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":17,"title":["Synthesis, Characterization, and Antioxidant Activity Evaluation of New N-Methyl Substituted Thiazole-Derived Polyphenolic Compounds"],"prefix":"10.3390","volume":"30","author":[{"given":"Alexandra C\u0103t\u0103lina","family":"Cornea","sequence":"first","affiliation":[{"name":"Department of Pharmaceutical Chemistry, \u201cIuliu Ha\u021bieganu\u201d University of Medicine and Pharmacy, 41 Victor Babe\u0219 Street, RO-400012 Cluj-Napoca, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9397-0388","authenticated-orcid":false,"given":"Gabriel","family":"Marc","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, \u201cIuliu Ha\u021bieganu\u201d University of Medicine and Pharmacy, 41 Victor Babe\u0219 Street, RO-400012 Cluj-Napoca, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ioana","family":"Ionu\u021b","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry, \u201cIuliu Ha\u021bieganu\u201d University of Medicine and Pharmacy, 41 Victor Babe\u0219 Street, RO-400012 Cluj-Napoca, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Cristina","family":"Moldovan","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry, \u201cIuliu Ha\u021bieganu\u201d University of Medicine and Pharmacy, 41 Victor Babe\u0219 Street, RO-400012 Cluj-Napoca, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8453-3642","authenticated-orcid":false,"given":"Anca","family":"Stana","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry, \u201cIuliu Ha\u021bieganu\u201d University of Medicine and Pharmacy, 41 Victor Babe\u0219 Street, RO-400012 Cluj-Napoca, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0297-7697","authenticated-orcid":false,"given":"Smaranda Dafina","family":"Oniga","sequence":"additional","affiliation":[{"name":"Department of Therapeutic Chemistry, \u201cIuliu Ha\u021bieganu\u201d University of Medicine and Pharmacy, 12 Ion Creang\u0103 Street, RO-400010 Cluj-Napoca, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2313-9350","authenticated-orcid":false,"given":"Adrian","family":"P\u00eern\u0103u","sequence":"additional","affiliation":[{"name":"National Institute for Research and Development of Isotopic and Molecular Technologies, 67-103 Donath Street, RO-400293 Cluj-Napoca, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0664-3387","authenticated-orcid":false,"given":"Laurian","family":"Vlase","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Technology and Biopharmaceutics, \u201cIuliu Ha\u021bieganu\u201d University of Medicine and Pharmacy, 41 Victor Babe\u0219 Street, RO-400012 Cluj-Napoca, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7660-9993","authenticated-orcid":false,"given":"Ilioara","family":"Oniga","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy, \u201cIuliu Ha\u021bieganu\u201d University of Medicine and Pharmacy, 12 Ion Creang\u0103 Street, RO-400010 Cluj-Napoca, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ovidiu","family":"Oniga","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry, \u201cIuliu Ha\u021bieganu\u201d University of Medicine and Pharmacy, 41 Victor Babe\u0219 Street, RO-400012 Cluj-Napoca, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2025,3,17]]},"reference":[{"key":"ref_1","first-page":"5594386","article-title":"A Comprehensive Review of Free Radicals, Oxidative Stress, and Antioxidants: Overview, Clinical Applications, Global Perspectives, Future Directions, and Mechanisms of Antioxidant Activity of Flavonoid Compounds","volume":"2024","author":"Tumilaar","year":"2023","journal-title":"J. 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