Supplementary material for the article: Lazić, A. M.; Mašulović, A. D.; Lađarević, J. M.; Valentić, N. V. Assessing the pharmacological potential of selected xanthene derivatives. Journal of the Serbian Chemical Society 2023, 88(9), 811-824. https://doi.org/10.2298/JSC230131035L
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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/polari...zability 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.
Кључне речи:
antioxidant activity / chemoinformatics prediction models / heterocycles / LSER analysis / solvatochromismИзвор:
Journal of the Serbian Chemical Society, 2023, 88, 9, S216-S241Издавач:
- Serbian Chemical Society
Финансирање / пројекти:
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200135 (Универзитет у Београду, Технолошко-металуршки факултет) (RS-MESTD-inst-2020-200135)
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200287 (Иновациони центар Технолошко-металуршког факултета у Београду доо) (RS-MESTD-inst-2020-200287)
Напомена:
- Related to: https://technorep.tmf.bg.ac.rs/handle/123456789/6809
- Supplementary material for: https://doi.org/10.2298/JSC230131035L
Повезане информације:
Институција/група
Tehnološko-metalurški fakultetTY - DATA AU - Lazić, Anita M. AU - Mašulović, Aleksandra D. AU - Lađarević, Jelena M. AU - Valentić, Nataša V. PY - 2023 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/6810 AB - 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. PB - Serbian Chemical Society T2 - Journal of the Serbian Chemical Society T1 - Supplementary material for the article: Lazić, A. M.; Mašulović, A. D.; Lađarević, J. M.; Valentić, N. V. Assessing the pharmacological potential of selected xanthene derivatives. Journal of the Serbian Chemical Society 2023, 88(9), 811-824. https://doi.org/10.2298/JSC230131035L EP - S241 IS - 9 SP - S216 VL - 88 UR - https://hdl.handle.net/21.15107/rcub_technorep_6810 ER -
@misc{ author = "Lazić, Anita M. and Mašulović, Aleksandra D. and Lađarević, Jelena M. and Valentić, Nataša V.", year = "2023", abstract = "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.", publisher = "Serbian Chemical Society", journal = "Journal of the Serbian Chemical Society", title = "Supplementary material for the article: Lazić, A. M.; Mašulović, A. D.; Lađarević, J. M.; Valentić, N. V. Assessing the pharmacological potential of selected xanthene derivatives. Journal of the Serbian Chemical Society 2023, 88(9), 811-824. https://doi.org/10.2298/JSC230131035L", pages = "S241-S216", number = "9", volume = "88", url = "https://hdl.handle.net/21.15107/rcub_technorep_6810" }
Lazić, A. M., Mašulović, A. D., Lađarević, J. M.,& Valentić, N. V.. (2023). Supplementary material for the article: Lazić, A. M.; Mašulović, A. D.; Lađarević, J. M.; Valentić, N. V. Assessing the pharmacological potential of selected xanthene derivatives. Journal of the Serbian Chemical Society 2023, 88(9), 811-824. https://doi.org/10.2298/JSC230131035L. in Journal of the Serbian Chemical Society Serbian Chemical Society., 88(9), S216-S241. https://hdl.handle.net/21.15107/rcub_technorep_6810
Lazić AM, Mašulović AD, Lađarević JM, Valentić NV. Supplementary material for the article: Lazić, A. M.; Mašulović, A. D.; Lađarević, J. M.; Valentić, N. V. Assessing the pharmacological potential of selected xanthene derivatives. Journal of the Serbian Chemical Society 2023, 88(9), 811-824. https://doi.org/10.2298/JSC230131035L. in Journal of the Serbian Chemical Society. 2023;88(9):S216-S241. https://hdl.handle.net/21.15107/rcub_technorep_6810 .
Lazić, Anita M., Mašulović, Aleksandra D., Lađarević, Jelena M., Valentić, Nataša V., "Supplementary material for the article: Lazić, A. M.; Mašulović, A. D.; Lađarević, J. M.; Valentić, N. V. Assessing the pharmacological potential of selected xanthene derivatives. Journal of the Serbian Chemical Society 2023, 88(9), 811-824. https://doi.org/10.2298/JSC230131035L" in Journal of the Serbian Chemical Society, 88, no. 9 (2023):S216-S241, https://hdl.handle.net/21.15107/rcub_technorep_6810 .