Abstract
Potentially biologically active functionally substituted thiadiazolopyrimidines were obtained via three-component condensation of 5-amino-1,3,4-thiadiazole-2-thiol with aromatic aldehydes and CH-acids (acetoacetic ester and malononitrile). Probable mechanisms for the formation of products are suggested. Quantum-chemical calculation of the aminating reagent molecule 5-amino-1,3,4-thiadiazole-2-thiol showed the preference of the amino group as the most active nucleophilic center. The study of molecular docking shows the potential for binding one of the representatives of the thiadizolopyrimidine series and cytidine deaminase. The structure of the new compounds was established using IR and 1H NMR spectroscopies.
References
N. S. El-Sayed, E. R. El-Bendary, S. M. El-Ashry, M. M. El-Kerdawy, Eur. J. Med. Chem., 2011, 46, 3714; DOI: https://doi.org/10.1016/j.ejmech.2011.05.037.
F. A. Ragab, H. I. Heiba, M. G. El-Gazzar, S. M. Abou-Seri, W. A. El-Sabbagh, R. M. El-Hazek, Med. Chem. Comm., 2016, 7, 2309; DOI: https://doi.org/10.1039/C6MD00367B.
U. K. Bhadraiah, V. Basavanna, D. M. Gurudatt, R. P. Shivalingappa, N. S. Lingegowda, S. Ningaiah, Biointerface Res. Appl. Chem., 2021, 11, 12925; DOI: https://doi.org/10.33263/BRIAC115.1292512936.
S. V. Tiwari, J. A. Seijas, M. P. Vazquez-Tato, A. P. Sarkate, D. K. Lokwani, A. P. G. Nikalje, Molecules, 2016, 21, 894; DOI: https://doi.org/10.3390/molecules21080894.
K. M. Dawood, T. A. Farghaly, Expert Opinion on Therapeutic Patents, 2017, 27, 477; DOI: https://doi.org/10.1080/13543776.2017.1272575.
S. A. Serkov, N. V. Sigai, N. N. Kostikova, A. E. Fedorov, G. A. Gazieva, Russ. Chem. Bull., 2022, 71, 1801; DOI: https://doi.org/10.1007/s11172-022-3592-1.
A. N. Proshin, T. P. Trofimov, O. N. Zefirova, I. V. Zhirkina, D. A. Skvortsov, S. O. Bachurin, Russ. Chem. Bull., 2021, 70, 510; DOI: https://doi.org/10.1007/s11172-021-3116-4.
A. N. Aksenov, M. M. Krayushkin, V. N. Yarovenko, Russ. Chem. Bull., 2021, 70, 510; DOI: https://doi.org/10.1007/s11172-021-3194-3.
D. V. Pasyukov, A. Yu. Chernenko, I. V. Lavrentev, V. A. Baydikova, M. E. Minyaev, O. A. Starovoytova, V. M. Chernyshev, Russ. Chem. Bull., 2022, 71, 993; DOI: https://doi.org/10.1007/s11172-022-3501-7.
A. A. Aly, A. A. Hassan, S. Bräse, M. A. Ibrahim, E. S. S. Abd Al-Latif, E. Spuling, M. Nieger, J. Sulfur. Chem., 2017, 38, 69; DOI: https://doi.org/10.1080/17415993.2016.1237637.
E. R. Rashed, M. G. El-Gazzar, M. A. El-Ghazaly, J. Pharm. Sci., 2014, 2, 1166.
E. A. Konstantinova, N. O. Vasilkova, in Mater. VII Vserosiiskoi nauchno-prakticheskoi konferentsii studentov i molodikh uchenikh, posvyaschenoi pamyati d.kh.n V.V Lukova “Khimiya: Dostizheniya i perspektivy” [In Proc. VII All-Russian Scientific and Practical Conference of Students and Young Scientists, dedicated to the memory of DSc V. V. Lukov “Chemistry: Achievements and Prospects”], Rostov-on-Don—Taganrog, 2022, 85–87 (in Russian).
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The work was carried out in accordance with the research plan of N. G. Chernyshevsky Saratov State University.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 73, No. 4, pp. 989–993, April, 2024.
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Konstantinova, E.A., Vasilkova, N.O. & Krivenko, A.P. Synthesis, structure, and formation paths of functionally substituted thiadiazolopyrimidines. Russ Chem Bull 73, 989–993 (2024). https://doi.org/10.1007/s11172-024-4212-z
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DOI: https://doi.org/10.1007/s11172-024-4212-z