Conjugated Oligo-Aromatic Compounds Bearing a 3,4,5-Trimethoxy Moiety: Investigation of Their Antioxidant Activity Correlated with a DFT Study
A series of heterocyclic compounds bearing the well-known free radical scavenging 3,4,5-trimethoxybenzyloxy group, was synthesized. The key compound 4-(3,4,5-trimethoxybenzyl-oxy)benzohydrazide was converted into thiosemicarbazide derivatives, which were subsequently cyclized with NaOH to provide 1,...
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| Format: | Article |
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MDPI AG
2016-02-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/21/2/224 |
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| author | Huda. S. Kareem Nurdiana Nordin Thorsten Heidelberg Azlina Abdul-Aziz Azhar Ariffin |
| author_facet | Huda. S. Kareem Nurdiana Nordin Thorsten Heidelberg Azlina Abdul-Aziz Azhar Ariffin |
| author_sort | Huda. S. Kareem |
| collection | DOAJ |
| description | A series of heterocyclic compounds bearing the well-known free radical scavenging 3,4,5-trimethoxybenzyloxy group, was synthesized. The key compound 4-(3,4,5-trimethoxybenzyl-oxy)benzohydrazide was converted into thiosemicarbazide derivatives, which were subsequently cyclized with NaOH to provide 1,2,4-triazole derivatives. Alternative treatment of the acid hydrazide with carbon disulfide in the presence of KOH led to the corresponding 1,3,4-oxadiazole and various alkylated derivatives. The newly synthesized compounds were purified and the structures of the products were elucidated and confirmed on the basis of their analytical and spectral data. Their antioxidant activities were evaluated using 2,2-diphenyl-1-picrylhydrazyl (DPPH•) and Ferric Reducing Antioxidant Power (FRAP) assays. The thiosemicarbazide derivatives were highly active in both antioxidant assays with the lowest IC50 value for DPPH radical scavenging. Theoretical calculations based on density functional theory (DFT) were performed to understand the relative importance of NH, SH and CH hydrogens on the radical scavenging activities of these compounds. |
| first_indexed | 2024-04-12T04:22:38Z |
| format | Article |
| id | doaj.art-a9ea794a9f4840d5a5d7c0c16f4d3151 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-12T04:22:38Z |
| publishDate | 2016-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-a9ea794a9f4840d5a5d7c0c16f4d31512022-12-22T03:48:11ZengMDPI AGMolecules1420-30492016-02-0121222410.3390/molecules21020224molecules21020224Conjugated Oligo-Aromatic Compounds Bearing a 3,4,5-Trimethoxy Moiety: Investigation of Their Antioxidant Activity Correlated with a DFT StudyHuda. S. Kareem0Nurdiana Nordin1Thorsten Heidelberg2Azlina Abdul-Aziz3Azhar Ariffin4Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603, MalaysiaDepartment of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603, MalaysiaDepartment of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603, MalaysiaDepartment of Molecular Medicine, Faculty of Medicine, University of Malaya, Kuala Lumpur 50603, MalaysiaDepartment of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603, MalaysiaA series of heterocyclic compounds bearing the well-known free radical scavenging 3,4,5-trimethoxybenzyloxy group, was synthesized. The key compound 4-(3,4,5-trimethoxybenzyl-oxy)benzohydrazide was converted into thiosemicarbazide derivatives, which were subsequently cyclized with NaOH to provide 1,2,4-triazole derivatives. Alternative treatment of the acid hydrazide with carbon disulfide in the presence of KOH led to the corresponding 1,3,4-oxadiazole and various alkylated derivatives. The newly synthesized compounds were purified and the structures of the products were elucidated and confirmed on the basis of their analytical and spectral data. Their antioxidant activities were evaluated using 2,2-diphenyl-1-picrylhydrazyl (DPPH•) and Ferric Reducing Antioxidant Power (FRAP) assays. The thiosemicarbazide derivatives were highly active in both antioxidant assays with the lowest IC50 value for DPPH radical scavenging. Theoretical calculations based on density functional theory (DFT) were performed to understand the relative importance of NH, SH and CH hydrogens on the radical scavenging activities of these compounds.http://www.mdpi.com/1420-3049/21/2/224thiosemicarbazidetriazoleoxadiazoleantioxidanthydrogen atom transfersingle electron transfer |
| spellingShingle | Huda. S. Kareem Nurdiana Nordin Thorsten Heidelberg Azlina Abdul-Aziz Azhar Ariffin Conjugated Oligo-Aromatic Compounds Bearing a 3,4,5-Trimethoxy Moiety: Investigation of Their Antioxidant Activity Correlated with a DFT Study Molecules thiosemicarbazide triazole oxadiazole antioxidant hydrogen atom transfer single electron transfer |
| title | Conjugated Oligo-Aromatic Compounds Bearing a 3,4,5-Trimethoxy Moiety: Investigation of Their Antioxidant Activity Correlated with a DFT Study |
| title_full | Conjugated Oligo-Aromatic Compounds Bearing a 3,4,5-Trimethoxy Moiety: Investigation of Their Antioxidant Activity Correlated with a DFT Study |
| title_fullStr | Conjugated Oligo-Aromatic Compounds Bearing a 3,4,5-Trimethoxy Moiety: Investigation of Their Antioxidant Activity Correlated with a DFT Study |
| title_full_unstemmed | Conjugated Oligo-Aromatic Compounds Bearing a 3,4,5-Trimethoxy Moiety: Investigation of Their Antioxidant Activity Correlated with a DFT Study |
| title_short | Conjugated Oligo-Aromatic Compounds Bearing a 3,4,5-Trimethoxy Moiety: Investigation of Their Antioxidant Activity Correlated with a DFT Study |
| title_sort | conjugated oligo aromatic compounds bearing a 3 4 5 trimethoxy moiety investigation of their antioxidant activity correlated with a dft study |
| topic | thiosemicarbazide triazole oxadiazole antioxidant hydrogen atom transfer single electron transfer |
| url | http://www.mdpi.com/1420-3049/21/2/224 |
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