Assessing the pharmacological potential of selected xanthene derivatives
A convenient and efficient approach toward the synthesis of seven aromatically substituted xanthendiones 1‒7 and one structurally-related xanthenone 8 through condensation of dimedone and the appropriate aromatic aldehyde is reported. Further, their chemical structure was confirmed by melting points...
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| Format: | Article |
| Language: | English |
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Serbian Chemical Society
2023-01-01
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| Series: | Journal of the Serbian Chemical Society |
| Subjects: | |
| Online Access: | https://doiserbia.nb.rs/img/doi/0352-5139/2023/0352-51392300035L.pdf |
| _version_ | 1797393707599659008 |
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| author | Lazić Anita M. Mašulović Aleksandra D. Lađarević Jelena M. Valentić Nataša V. |
| author_facet | Lazić Anita M. Mašulović Aleksandra D. Lađarević Jelena M. Valentić Nataša V. |
| author_sort | Lazić Anita M. |
| collection | DOAJ |
| description | A convenient and efficient approach toward the synthesis of seven aromatically substituted xanthendiones 1‒7 and one structurally-related xanthenone 8 through condensation of dimedone and the appropriate aromatic aldehyde is reported. Further, their chemical structure was confirmed by melting points, elemental analysis, FT-IR, 1H-, 13C-NMR and UV–Vis spectroscopic methods. The relationship between the chemical structure and pharmacological activity was determined empirically using appropriate software packages and in vitro using the 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid (ABTS) method. The results of in silico prediction suggested that all investigated compounds possess good oral bioavailability. The results of the ABTS assay indicate that five compounds possess the ability to scavenge the ABTS•+ radical cation. Based on the comparison of the IC50 values, the activity of the compounds was found to be as follows: 6 > 1 > 7 > 2 > 8. The effects of solvent dipolarity/ polarizability and solute solvent–hydrogen-bonding interactions on the shifts of the absorption maxima were rationalized by means of the linear solvation energy relationship concepts proposed by Kamlet–Taft and Catalán. |
| first_indexed | 2024-03-09T00:07:43Z |
| format | Article |
| id | doaj.art-f47051fa909c46a6993219b32b3f26ca |
| institution | Directory Open Access Journal |
| issn | 0352-5139 1820-7421 |
| language | English |
| last_indexed | 2024-03-09T00:07:43Z |
| publishDate | 2023-01-01 |
| publisher | Serbian Chemical Society |
| record_format | Article |
| series | Journal of the Serbian Chemical Society |
| spelling | doaj.art-f47051fa909c46a6993219b32b3f26ca2023-12-12T13:08:08ZengSerbian Chemical SocietyJournal of the Serbian Chemical Society0352-51391820-74212023-01-0188981182410.2298/JSC230131035L0352-51392300035LAssessing the pharmacological potential of selected xanthene derivativesLazić Anita M.0https://orcid.org/0000-0003-4855-3782Mašulović Aleksandra D.1https://orcid.org/0000-0002-5279-7694Lađarević Jelena M.2https://orcid.org/0000-0002-5554-7295Valentić Nataša V.3https://orcid.org/0000-0002-5466-7738Innovation Center, Faculty of Technology and Metallurgy, Belgrade, SerbiaInnovation Center, Faculty of Technology and Metallurgy, Belgrade, SerbiaUniversity of Belgrade, Faculty of Technology and Metallurgy, Belgrade, SerbiaUniversity of Belgrade, Faculty of Technology and Metallurgy, Belgrade, SerbiaA convenient and efficient approach toward the synthesis of seven aromatically substituted xanthendiones 1‒7 and one structurally-related xanthenone 8 through condensation of dimedone and the appropriate aromatic aldehyde is reported. Further, their chemical structure was confirmed by melting points, elemental analysis, FT-IR, 1H-, 13C-NMR and UV–Vis spectroscopic methods. The relationship between the chemical structure and pharmacological activity was determined empirically using appropriate software packages and in vitro using the 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid (ABTS) method. The results of in silico prediction suggested that all investigated compounds possess good oral bioavailability. The results of the ABTS assay indicate that five compounds possess the ability to scavenge the ABTS•+ radical cation. Based on the comparison of the IC50 values, the activity of the compounds was found to be as follows: 6 > 1 > 7 > 2 > 8. The effects of solvent dipolarity/ polarizability and solute solvent–hydrogen-bonding interactions on the shifts of the absorption maxima were rationalized by means of the linear solvation energy relationship concepts proposed by Kamlet–Taft and Catalán.https://doiserbia.nb.rs/img/doi/0352-5139/2023/0352-51392300035L.pdfheterocycleschemoinformatics prediction modelsantioxidant activitylser analysissolvatochromism |
| spellingShingle | Lazić Anita M. Mašulović Aleksandra D. Lađarević Jelena M. Valentić Nataša V. Assessing the pharmacological potential of selected xanthene derivatives Journal of the Serbian Chemical Society heterocycles chemoinformatics prediction models antioxidant activity lser analysis solvatochromism |
| title | Assessing the pharmacological potential of selected xanthene derivatives |
| title_full | Assessing the pharmacological potential of selected xanthene derivatives |
| title_fullStr | Assessing the pharmacological potential of selected xanthene derivatives |
| title_full_unstemmed | Assessing the pharmacological potential of selected xanthene derivatives |
| title_short | Assessing the pharmacological potential of selected xanthene derivatives |
| title_sort | assessing the pharmacological potential of selected xanthene derivatives |
| topic | heterocycles chemoinformatics prediction models antioxidant activity lser analysis solvatochromism |
| url | https://doiserbia.nb.rs/img/doi/0352-5139/2023/0352-51392300035L.pdf |
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