Abstract
New 3,5-disubstituted-1,2,4-thiadiazoles were synthesized and together with a series of their analogs obtained earlier were tested for cytotoxic activity to breast adenocarcinoma MCF-7 and lung carcinoma A 549 cells. The selectivity of cytotoxic action was determined in comparison to etiologically noncancerous breast epithelial cells MCF-10A and lung fibroblasts VA13. From five- to six-fold selectivity of cytotoxic action was revealed for 3,4-dichlorophenyl-{3-[2-(2-morpholin-4-ylethylamino)propyl]-[1,2,4]thiadiazol-5-yl}amine and (2-{5-[(4-diethylami-nobenzyl)pyridin-3-ylmethylamino]-[1,2,4]thiadiazol-3-yl}-1-methylvinyl)-(2,2,6,6-tetra-methylpiperidin-4-yl)amine in the pairs A 549/VA13 and MCF-7/MCF-10A, respectively. Some structure—property relationships for the compounds under study were discussed.
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S. Bendels, C. Bissantz, B. Fasching, G. Gerebtzoff, W. Guba, M. Kansy, J. Migeon, S. Mohr, J.-U. Peters, F. Tillier, R. Wyler, C. Lerner, C. Kramer, H. Richter, S. Roberts, J. Pharm. Tox. Methods, 2019, 99, 106609.
O. M. Lage, M. C. Ramos, R. Calisto, E. Almeida, V. Vasconcelos, F. Vicente, Mar. Drugs, 2018, 16, 279.
W. R. J. D. Galloway, A. Isidro-Llobet, D. R. Spring, Nat. Commun., 2010, 1, 80.
M. M. Krayushkin, V. N. Yarovenko, I. V. Zavarzin, Russ. Chem. Bull., 2019, 68, 1143.
N. A. Pulina, F. V. Sobin, T. A. Yushkova, V. V. Novikova, Russ. Chem. Bull., 2019, 68, 628.
I. V. Serkov, A. N. Proshin, L. N. Petrova, S. O. Bachurin, Dokl. Chem. (Engl. Transl.), 2010, 435, 311.
V. V. Grigoriev, G. F. Makhaeva, A. N. Proshin, N. V. Kovaleva, E. V. Rudakova, N. P. Boltneva, A. V. Gabrel’yan, B. V. Lednev, S. O. Bachurin, Russ. Chem. Bull., 2017, 66, 1308.
G. F. Makhaeva, A. N. Proshin, N. P. Boltneva, E. V. Rudakova, N. V. Kovaleva, O. G. Serebryakova, I. V. Serkov, S. O. Bachurin, Russ. Chem. Bull., 2016, 65, 1586.
Pat. RF No. 2011105263 (WO 2012/050484 A2) (in Russian).
Pat. RF No. 2536824 (RU 2 536 824 C1) (in Russian).
S. Hoelder, P. A. Clarke, P. Workman, Mol. Oncol., 2012, 6, 155.
F. M. Balis, J. Natl. Cancer Inst., 2002, 94, 78.
M. G. Akimov, N. M. Gretskaya, V. A. Karnoukhova, I. V. Serkov, A. N. Proshin, V. Yu. Shtratnikova, V. V. Bezuglov, Biomed. Khim. [Biomed. Chem.], 2014, 60, 473 (in Russian).
A. N. Proshin, T. P. Trofimova, O. N. Zefirova, L. N. Petrova, D. A. Skvortsov, S. O. Bachurin, Russ. Chem. Bull., 2019, 68, 2279.
M. A. Kalinina, D. A. Skvortsov, M. P. Rubtsova, E. S. Komarova, O. A. Dontsova, Mol. Imaging Biol., 2018, 20, 368.
A. Kamboj, H. Randhawa, J. Pharm. Res., 2012, 5, 2676.
The Practice of Medicinal Chemistry, 2nd ed., Ed. C. G. Wermuth, Acad. Press, Amsterdam, Boston, 2003, 768 pp.
O. N. Zefirova, K. V. Balakin, M. Yu. Krasavin, V. A. Palyulin, V. V. Poroykov, E. V. Radchenko, N. F. Salakhutdinov, A. A. Spasov, V. P. Fisenko, S. O. Bachurin, Russ. Chem. Bull., 2019, 68, 2381.
I. Muegge, Med. Res. Rev., 2003, 23, 302.
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The research was carried out in the framework of the Russian state assignment of the Ministry of Science and Higher Education of the Russian Federation (Topic No. 0090-2020-0001). Screening of cytotoxicity of compounds was financially supported by the Russian Foundation for Basic Research (Project No. 18-29-08060_mk).
This work does not involve human participants and animal subjects.
The authors declare that there is no conflict of interest.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 510–514, March, 2021.
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Proshin, A.N., Trofimova, T.P., Zefirova, O.N. et al. Screening of a series of 3,5-disubstituted 1,2,4-thiadiazoles for selectivity of cytotoxic action to cancer cells. Russ Chem Bull 70, 510–514 (2021). https://doi.org/10.1007/s11172-021-3116-4
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DOI: https://doi.org/10.1007/s11172-021-3116-4