New Phenolic Derivatives of Thiazolidine-2,4-dione with Antioxidant and Antiradical Properties: Synthesis, Characterization, In Vitro Evaluation, and Quantum Studies
Oxidative stress has been incriminated in the physiopathology of many diseases, such as diabetes, cancer, atherosclerosis, and cardiovascular and neurodegenerative diseases. There is a great interest in developing new antioxidants that could be useful for preventing and treating conditions for which...
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| Format: | Article |
| Language: | English |
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MDPI AG
2019-05-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/24/11/2060 |
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| author | Gabriel Marc Anca Stana Smaranda Dafina Oniga Adrian Pîrnău Laurian Vlase Ovidiu Oniga |
| author_facet | Gabriel Marc Anca Stana Smaranda Dafina Oniga Adrian Pîrnău Laurian Vlase Ovidiu Oniga |
| author_sort | Gabriel Marc |
| collection | DOAJ |
| description | Oxidative stress has been incriminated in the physiopathology of many diseases, such as diabetes, cancer, atherosclerosis, and cardiovascular and neurodegenerative diseases. There is a great interest in developing new antioxidants that could be useful for preventing and treating conditions for which oxidative stress is suggested as the root cause. The thiazolidine-2,4-dione derivatives have been reported to possess various pharmacological activities and the phenol moiety is known as a pharmacophore in many naturally occurring and synthetic antioxidants. Twelve new phenolic derivatives of thiazolidine-2,4-dione were synthesized and physicochemically characterized. The antioxidant capacity of the synthesized compounds was assessed through several in vitro antiradical, electron transfer, and Fe<sup>2+</sup> chelation assays. The top polyphenolic compounds <b>5f</b> and <b>5l</b> acted as potent antiradical and electron donors, with activity comparable to the reference antioxidants used. The ferrous ion chelation capacity of the newly synthesized compounds was modest. Several quantum descriptors were calculated in order to evaluate their influence on the antioxidant and antiradical properties of the compounds and the chemoselectivity of the radical generation reactions has been evaluated. The correlation with the energetic level of the frontier orbitals partially explained the antioxidant activity, whereas a better correlation was found while evaluating the O−H bond dissociation energy of the phenolic groups. |
| first_indexed | 2024-12-20T20:49:46Z |
| format | Article |
| id | doaj.art-dffb22b7c58a46e6ab19237318417387 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-20T20:49:46Z |
| publishDate | 2019-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-dffb22b7c58a46e6ab192373184173872022-12-21T19:26:57ZengMDPI AGMolecules1420-30492019-05-012411206010.3390/molecules24112060molecules24112060New Phenolic Derivatives of Thiazolidine-2,4-dione with Antioxidant and Antiradical Properties: Synthesis, Characterization, In Vitro Evaluation, and Quantum StudiesGabriel Marc0Anca Stana1Smaranda Dafina Oniga2Adrian Pîrnău3Laurian Vlase4Ovidiu Oniga5Department of Pharmaceutical Chemistry, “Iuliu Hațieganu” University of Medicine and Pharmacy, 41 Victor Babeș Street, RO-400012 Cluj-Napoca, RomaniaDepartment of Pharmaceutical Chemistry, “Iuliu Hațieganu” University of Medicine and Pharmacy, 41 Victor Babeș Street, RO-400012 Cluj-Napoca, RomaniaDepartment of Therapeutic Chemistry, “Iuliu Hațieganu” University of Medicine and Pharmacy, 12 Ion Creangă Street, RO-400010 Cluj-Napoca, RomaniaNational Institute for Research and Development of Isotopic and Molecular Technologies, RO-400293 Cluj-Napoca, RomaniaDepartment of Pharmaceutical Technology and Biopharmaceutics, “Iuliu Hațieganu” University of Medicine and Pharmacy, 41 Victor Babeș Street, RO-400012 Cluj-Napoca, RomaniaDepartment of Pharmaceutical Chemistry, “Iuliu Hațieganu” University of Medicine and Pharmacy, 41 Victor Babeș Street, RO-400012 Cluj-Napoca, RomaniaOxidative stress has been incriminated in the physiopathology of many diseases, such as diabetes, cancer, atherosclerosis, and cardiovascular and neurodegenerative diseases. There is a great interest in developing new antioxidants that could be useful for preventing and treating conditions for which oxidative stress is suggested as the root cause. The thiazolidine-2,4-dione derivatives have been reported to possess various pharmacological activities and the phenol moiety is known as a pharmacophore in many naturally occurring and synthetic antioxidants. Twelve new phenolic derivatives of thiazolidine-2,4-dione were synthesized and physicochemically characterized. The antioxidant capacity of the synthesized compounds was assessed through several in vitro antiradical, electron transfer, and Fe<sup>2+</sup> chelation assays. The top polyphenolic compounds <b>5f</b> and <b>5l</b> acted as potent antiradical and electron donors, with activity comparable to the reference antioxidants used. The ferrous ion chelation capacity of the newly synthesized compounds was modest. Several quantum descriptors were calculated in order to evaluate their influence on the antioxidant and antiradical properties of the compounds and the chemoselectivity of the radical generation reactions has been evaluated. The correlation with the energetic level of the frontier orbitals partially explained the antioxidant activity, whereas a better correlation was found while evaluating the O−H bond dissociation energy of the phenolic groups.https://www.mdpi.com/1420-3049/24/11/2060thiazolidine-2,4-dionephenolsalicylamideantioxidantantiradicalquantum descriptors |
| spellingShingle | Gabriel Marc Anca Stana Smaranda Dafina Oniga Adrian Pîrnău Laurian Vlase Ovidiu Oniga New Phenolic Derivatives of Thiazolidine-2,4-dione with Antioxidant and Antiradical Properties: Synthesis, Characterization, In Vitro Evaluation, and Quantum Studies Molecules thiazolidine-2,4-dione phenol salicylamide antioxidant antiradical quantum descriptors |
| title | New Phenolic Derivatives of Thiazolidine-2,4-dione with Antioxidant and Antiradical Properties: Synthesis, Characterization, In Vitro Evaluation, and Quantum Studies |
| title_full | New Phenolic Derivatives of Thiazolidine-2,4-dione with Antioxidant and Antiradical Properties: Synthesis, Characterization, In Vitro Evaluation, and Quantum Studies |
| title_fullStr | New Phenolic Derivatives of Thiazolidine-2,4-dione with Antioxidant and Antiradical Properties: Synthesis, Characterization, In Vitro Evaluation, and Quantum Studies |
| title_full_unstemmed | New Phenolic Derivatives of Thiazolidine-2,4-dione with Antioxidant and Antiradical Properties: Synthesis, Characterization, In Vitro Evaluation, and Quantum Studies |
| title_short | New Phenolic Derivatives of Thiazolidine-2,4-dione with Antioxidant and Antiradical Properties: Synthesis, Characterization, In Vitro Evaluation, and Quantum Studies |
| title_sort | new phenolic derivatives of thiazolidine 2 4 dione with antioxidant and antiradical properties synthesis characterization in vitro evaluation and quantum studies |
| topic | thiazolidine-2,4-dione phenol salicylamide antioxidant antiradical quantum descriptors |
| url | https://www.mdpi.com/1420-3049/24/11/2060 |
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