Hybridization of Aminoadamantanes with Cinnamic Acid Analogues and Elucidation of Their Antioxidant Profile
A series of seventeen cinnamic acid hybrids (4ai–ci) were obtained through an amidation of aminoadamantanes (amantadine, rimantadine, and memantine) with mixed anhydride generated from different substituted cinnamic acid and ethyl chloroformate. 1H NMR, 13C NMR, IR, and HRMS were used for the confir...
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| Language: | English |
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Wiley
2022-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2022/7582587 |
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| author | Maya Chochkova Almira Georgieva Tsvetelina Ilieva Madlena Andreeva Georgi Pramatarov Nejc Petek Petranka Petrova Martin Štícha Yavor Mitrev Jurij Svete |
| author_facet | Maya Chochkova Almira Georgieva Tsvetelina Ilieva Madlena Andreeva Georgi Pramatarov Nejc Petek Petranka Petrova Martin Štícha Yavor Mitrev Jurij Svete |
| author_sort | Maya Chochkova |
| collection | DOAJ |
| description | A series of seventeen cinnamic acid hybrids (4ai–ci) were obtained through an amidation of aminoadamantanes (amantadine, rimantadine, and memantine) with mixed anhydride generated from different substituted cinnamic acid and ethyl chloroformate. 1H NMR, 13C NMR, IR, and HRMS were used for the confirmation of the structures of the synthesized hybrids. Moreover, the antioxidant profiles of amides were estimated as per five different in vitro methods: 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2′-azinobis-3-ethylbenzothiazoline-6-sulfonic acid cation radical (ABTS⁺), ferric reducing antioxidant power (FRAP), cupric reducing antioxidant capacity (CUPRAC) assay, and inhibition of Fe(III)/asc induced lipid peroxidation (LP) in brain homogenate. For comparison, caffeic acid (CaffA), known as a potent naturally occurring antioxidant, was used as a reference compound in our study. The results revealed that the most prominent antioxidant activity was demonstrated by compound 4b2, with excellent CUPRAC, FRAP, scavenging ABTS+˙ potential, and inhibition of Fe/asc–induced LP, followed by 4c6 > 4a6 > CaffA > 4c5 and 4a5 > 4a7. Overall, the results suggest that the hybrids (4b2, 4c6, and 4a6) consisting of a caffeoyl moiety and lipophilic adamantane core endow the molecules with the higher antioxidant activity than their parent compound (caffeic acid), especially against LP. Thus, these promising antioxidants could have beneficial effects in various pathological conditions, where oxidative stress is implicated. |
| format | Article |
| id | doaj-art-3dd3e2e3a7314bb59d4b17a383fa381f |
| institution | Kabale University |
| issn | 2090-9071 |
| language | English |
| publishDate | 2022-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-3dd3e2e3a7314bb59d4b17a383fa381f2025-02-03T05:57:55ZengWileyJournal of Chemistry2090-90712022-01-01202210.1155/2022/7582587Hybridization of Aminoadamantanes with Cinnamic Acid Analogues and Elucidation of Their Antioxidant ProfileMaya Chochkova0Almira Georgieva1Tsvetelina Ilieva2Madlena Andreeva3Georgi Pramatarov4Nejc Petek5Petranka Petrova6Martin Štícha7Yavor Mitrev8Jurij Svete9Faculty of Mathematics and Natural SciencesLaboratory of Free Radical ProcessesFaculty of Mathematics and Natural SciencesLaboratory of Free Radical ProcessesLaboratory of Free Radical ProcessesFaculty of Chemistry and Chemical TechnologyFaculty of Mathematics and Natural SciencesCharles UniversityInstitute of Organic Chemistry with Centre of PhytochemistryFaculty of Chemistry and Chemical TechnologyA series of seventeen cinnamic acid hybrids (4ai–ci) were obtained through an amidation of aminoadamantanes (amantadine, rimantadine, and memantine) with mixed anhydride generated from different substituted cinnamic acid and ethyl chloroformate. 1H NMR, 13C NMR, IR, and HRMS were used for the confirmation of the structures of the synthesized hybrids. Moreover, the antioxidant profiles of amides were estimated as per five different in vitro methods: 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2′-azinobis-3-ethylbenzothiazoline-6-sulfonic acid cation radical (ABTS⁺), ferric reducing antioxidant power (FRAP), cupric reducing antioxidant capacity (CUPRAC) assay, and inhibition of Fe(III)/asc induced lipid peroxidation (LP) in brain homogenate. For comparison, caffeic acid (CaffA), known as a potent naturally occurring antioxidant, was used as a reference compound in our study. The results revealed that the most prominent antioxidant activity was demonstrated by compound 4b2, with excellent CUPRAC, FRAP, scavenging ABTS+˙ potential, and inhibition of Fe/asc–induced LP, followed by 4c6 > 4a6 > CaffA > 4c5 and 4a5 > 4a7. Overall, the results suggest that the hybrids (4b2, 4c6, and 4a6) consisting of a caffeoyl moiety and lipophilic adamantane core endow the molecules with the higher antioxidant activity than their parent compound (caffeic acid), especially against LP. Thus, these promising antioxidants could have beneficial effects in various pathological conditions, where oxidative stress is implicated.http://dx.doi.org/10.1155/2022/7582587 |
| spellingShingle | Maya Chochkova Almira Georgieva Tsvetelina Ilieva Madlena Andreeva Georgi Pramatarov Nejc Petek Petranka Petrova Martin Štícha Yavor Mitrev Jurij Svete Hybridization of Aminoadamantanes with Cinnamic Acid Analogues and Elucidation of Their Antioxidant Profile Journal of Chemistry |
| title | Hybridization of Aminoadamantanes with Cinnamic Acid Analogues and Elucidation of Their Antioxidant Profile |
| title_full | Hybridization of Aminoadamantanes with Cinnamic Acid Analogues and Elucidation of Their Antioxidant Profile |
| title_fullStr | Hybridization of Aminoadamantanes with Cinnamic Acid Analogues and Elucidation of Their Antioxidant Profile |
| title_full_unstemmed | Hybridization of Aminoadamantanes with Cinnamic Acid Analogues and Elucidation of Their Antioxidant Profile |
| title_short | Hybridization of Aminoadamantanes with Cinnamic Acid Analogues and Elucidation of Their Antioxidant Profile |
| title_sort | hybridization of aminoadamantanes with cinnamic acid analogues and elucidation of their antioxidant profile |
| url | http://dx.doi.org/10.1155/2022/7582587 |
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