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Synthesis, Antifungal, and Antioxidant Evaluation of New Class of Thiazolo[3,2-a]pyrimidine and Pyrimido[5,4-d]thiazolo[3,2-a]pyrimidine Derived from α,α-Ketene Dithioacetals as Five and Six-membered Heterocycles Analogues.
- Source :
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Russian Journal of Bioorganic Chemistry . Oct2023, Vol. 49 Issue 5, p1119-1136. 18p. - Publication Year :
- 2023
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Abstract
- A novel series of heterocyclic compounds containing thiazolo[3,2-a]pyrimidine and pyrimido[5,4-d]thiazolo[3,2-a]pyrimidine analogues were designed and synthesized starting from α,α-ketene dithioacetals (I), and their structures were confirmed by elemental analysis, IR, 1H NMR, and 13C NMR. In our study, we also present optimization of the synthetic method along with a biological evaluation of these newly synthesized compounds as antioxidants and antifungal. Preliminary bioassay showed that most of them exhibited certain-to-excellent antioxidant and antifungal activity. Among all the evaluated compounds, it was found that some showed significant antioxidant activity at 10 µg/mL while the others exhibited better antifungalal activity at 100 µg/mL. Thiazolo[3,2-a]pyrimidines (IVa–IVb) and (IVc–IVd) showed higher than 80% inhibition activity against C. arachidicola and P. infestans respectively whereas the thiazolo[3,2-a]pyrimidines (VIc–VId) showed maximum activity against B. cinerea and C. arachidicola, as for the tested pyrimido[5,4-d]thiazolo[3,2-a]pyrimidines (IXc–IXd) against G. zeae, P. piricola, and P. sasakii. In particular, thiazolo[3,2-a]pyrimidines (IVc–IVd) exhibited outstanding activity (> 90%) against G. zeae. Among all the evaluated compounds, it was found that some showed significant antioxidant activity at 10 µg/mL and the maximum DPPH radical scavenging activity was observed with synthetic thiazolo[3,2-a]pyrimidines (VIIc–VIId) and pyrimido[5,4-d]thiazolo[3,2-a]pyrimidine (IXc–IXd), especially pyrimido[5,4-d]thiazolo[3,2-a]pyrimidine (IXc) which possessed the highest antioxidant activity in comparable to that of standard vitamin C at similar concentration. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 10681620
- Volume :
- 49
- Issue :
- 5
- Database :
- Academic Search Index
- Journal :
- Russian Journal of Bioorganic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 170040589
- Full Text :
- https://doi.org/10.1134/S1068162023050199