RAS Chemistry & Material ScienceЖурнал общей химии Russian Journal of General Chemistry

  • ISSN (Print) 0044-460X
  • ISSN (Online) 3034-5596

Synthesis and study of some properties of new tetrazole-containing derivatives of morpholin-4-yl-1,3,5-triazine and 4-methylpiperidin-1-yl-1,3,5-triazine

PII
10.31857/S0044460X23050050-1
DOI
10.31857/S0044460X23050050
Publication type
Article
Status
Published
Authors
Volume/ Edition
Volume 93 / Issue number 5
Pages
695-710
Abstract
New tetrazole-containing derivatives of morpholin-4-yl-1,3,5-triazine and 4-methylpiperidin-1-yl-1,3,5-triazine were synthesized. Cytotoxic activity of the compounds obtained against human liver tumor cell lines Huh-7 and human lung A549 was studied by the MTT test. It was shown that these substances do not exhibit a pronounced cytotoxic effect. The most significant antitumor activity was shown by 1,3,5-triazine containing 5-phenyltetrazol-2-ylacetohydrazide fragment and 4-methylpiperidine ring as substituents, as well as 1,3,5-triazine containing 5-methyl-1 H -tetrazol-1-ylacetohydrazide fragment and two morpholine rings. For these compounds, the interaction with DNA was studied by UV spectroscopy. For N ’-(4,6-dimorpholino-1,3,5-triazin-2-yl)-2-(5-methyl-1 H -tetrazol-1-yl)acetohydrazide, the DNA binding constant was determined ( K bin 9.02× 104 M.-1) and studied the ability to inhibit the tyrosine kinase domain of surface receptors. It was shown that the studied tetrazole-containing derivatives of 1,3,5-triazine do not exhibit antioxidant properties with respect to NO-radicals and do not cause photoinduced hemolysis.
Keywords
1,3,5-триазин 5-арилтетразолы 5-метил-1H-тетразол-1-илацетогидразид 5-фенил-2H-тетразол-2-илацетогидразид цитотоксическая активность ингибирующая активность
Date of publication
17.09.2025
Year of publication
2025
Number of purchasers
0
Views
13

References

  1. 1. Singla P., Luxami V., Paul K. // Eur. J. Med. Chem. 2015. Vol. 18. N 102. P. 39. doi 10.1016/j.ejmech.2015.07.037
  2. 2. Cascioferro S., Parrino B., Spanò V., Carbone A., Montalbano A., Barraja P., Diana P., Cirrincione G. // Eur. J. Med. Chem. 2017. Vol. 15. N 142. P. 523. doi 10.1016/j.ejmech.2017.09.035
  3. 3. Maliszewski D., Drozdowska D. // Pharmaceuticals. 2022. Vol. 15. N 2. P. 221. doi 10.3390/ph15020221
  4. 4. Миколайчук О.В., Шаройко В.В., Попова Е.А., Протас А.В., Фонин А.В., Ануфриков Ю.А., Малкова А.М., Шманёва Н.Т., Островский В.А., Семенов К.Н. // Изв. АН. Сер. хим. 2022. № 5. С. 1050
  5. 5. Mikolaichuk O.V., Sharoyko V.V., Popova E.A., Protas A.V., Fonin A.V., Anufrikov Y.A., Malkova A.M., Shmaneva N.T., Ostrovskii V.A., Molchanov O.E., Maistrenko D.N., Semenov K.N. // Russ. Chem. Bull. 2022 Vol. 71. P. 1050. doi 10.1007/s11172-022-3507-1
  6. 6. Konstantinov S.M., Berger M.R. Encyclopedia of Molecular Pharmacology. Berlin: Springer, 2008. P. 53. doi 10.1007/978-3-540-38918-7_178
  7. 7. Попова Е.А., Трифонов Р.Е., Островский В.А. // Усп. хим. 2019. № 6. С. 644
  8. 8. Popova E.A., Trifonov R.E., Ostrovskii V.A. // Russ. Chem. Rev. 2019. Vol. 88. P. 644. doi 10.1070/RCR4864
  9. 9. Островский В.А., Трифонов Р.Е., Попова Е.А. // Изв. АН. Сер. хим. 2012. Т. 61. С. 765
  10. 10. Ostrovskii V.A., Trifonov R.E., Popova E.A. // Russ. Chem. Bull. 2012. Vol. 61. N 4. P. 768. doi 10.1007/s11172-012-0108-4
  11. 11. Ostrovskii V.A., Popova E.A., Trifonov R.E. // Compr. Heterocycl. Chem. 2022. P. 182. doi 10.1016/B978-0- 12-818655-8.00131-1
  12. 12. Herr R.J. // Bioorg. Med. Chem. 2002. Vol. 10. N 11. P. 3379. doi 10.1016/S0968-0896(02)00239-0
  13. 13. Пат. RU (11) 2 124 020(13) C1 (1993). Роспатент // 1998. 22 О 393
  14. 14. Shin-ichi Y., Yasuhisa F., Ichiro K., Hisashi Y., Toshiyuki M., Hiroaki G., Shuichi H., Kanami Y., Takao Y. // JNCI. 2006. Vol. 98. N 8. P. 545. doi 10.1093/jnci/djj133
  15. 15. Miller M.S., Pinson J.A., Zheng Z., Jennings I.G., Thompson P.E. // Bioorg. Med. Chem. Lett. 2013. Vol. 23. N 3. P. 802-5. doi 10.1016/j.bmcl.2012.11.076
  16. 16. Norman M.H., Andrews K.L., Bo Y.X.Y., Booker S.K., Caenepeel S., Cee V.J., D'Angelo N.D., Freeman D.J., Herberich B.J., Hong F.T., Jackson C.L.M., Jiang J., Lanman B.A., Liu L.B., McCarter J.D., Mullady E.L., Nishimura N., Pettus L.H., Reed A.B., Miguel T.S., Smith A.L., Stec M.M., Tadesse S., Tasker A., Aidasani D., Zhu X.C., Subramanian R., Tamayo N.A., Wang L., Whittington D.A., Wu B., Wu T., Wurz R.P., Yang K., Zalameda L., Zhang N., Hughes P.E. // J. Med. Chem. 2012. Vol. 55. P. 7796. doi 10.1021/jm300846z
  17. 17. Dehnhardt C.M., Venkatesan A.M., Chen Z., Delos-Santos E., Ayral-Kaloustian S., Brooijmans N., Yu K., Hollander I., Feldberg L., Lucas J., Mallon R. // Bioorg. Med. Chem. Lett. 2011. Vol. 16. P. 4773. doi 10.1016/j.bmcl.2011.06.063
  18. 18. Миколайчук О.В., Протас А.В., Попова Е.А., Молчанов О.Е., Майстренко Д.Н., Островский В.А., Павлюкова Ю.Н., Шаройко В.В., Семенов К.Н. // ЖОХ. 2022. № 9. С. 1368. doi 10.31857/S0044460X22090050
  19. 19. Mikolaichuk O.V., Protas A.V., Popova E.A., Molchanov O.E., Maistrenko D.N., Ostrovskii V.A., Pavlyukova Y.N., Sharoyko V.V., Semenov K.N. // Russ. J. Gen. Chem. 2022. Vol. 92. P. 1621. doi 10.1134/S1070363222090055
  20. 20. Sirajuddin M., Ali S., Badshah A. // J. Photochem. Photobiol. (B). 2013. Vol. 124. P. 1. doi 10.1016/j.jphotobiol.2013.03.013
  21. 21. Миколайчук О.В., Протас А.В., Попова Е.А., Мухаметшина А.В., Овсепян Г.К., Трифонов Р.Е. // Изв. АН. Сер. хим. 2018. C. 1312
  22. 22. Mikolaichuk O.V., Protas A.V., Popova E.A., Mukhametshina A.V., Ovsepyan G.K., Trifonov R.E. // Russ. Chem. Bull. 2018. Vol. 67. P. 1312. doi 10.1007/s11172-018-2217-1
  23. 23. Topală T., Bodoki A., Oprean L., Oprean R. // Farmacia. 2014. Vol. 62. P. 1049.
  24. 24. García-Ramos J.C., Galindo-Murillo R., Cortés-Guzmán F., Azuara L.R. // J. Mex. Chem. Soc. 2013. Vol. 57. N 3. P. 245 doi 10.29356/jmcs.v57i3.213
  25. 25. Wolfe A., Jr G.H.S., Meehan T. // Society. 2002. Vol. 26. P. 6392.
  26. 26. Raghu M.S., Pradeep Kumar C.B., Prashanth M.K., Yogesh Kumar K., Prathibha B.S., Kanthimathi G., Alissa S.A., Alghulikah H.A., Osman S.M. // New J. Chem. 2021 Vol. 45. P. 13909. doi 10.1039/D1NJ02419A
  27. 27. Mikolaichuk O.V., Popova E.A., Protas A.V., Rakipov I.T., Nerukh D.A., Petrov A.V., Charykov N.A., Ageev S.V., Tochilnikov G.V., Zmitrichenko I.G., Stukov A.N., Semenov K.N, Sharoyko V.V. // J. Mol. Liq. 2022. Vol. 356. Art. no. 119043. doi 10.1016/j. molliq.2022.119043
  28. 28. Laemmli U.K. // Nature. 1970 Vol. 227. N 5259. P. 680. doi 10.1038/227680a0
  29. 29. Abdelhalim A.O.E., Sharoyko V. V., Meshcheriakov A.A., Martynova S.D., Ageev S.V., Iurev G.O., Mulla H.Al, Petrov A.V., Solovtsova I.L., Vasina L.V., Murin I.V., Semenov K.N. // Nanomed. Nanotechnol. Biol. Med. 2020. Vol. 29 P. 102284. doi 10.1016/j.nano.2020.102284
  30. 30. Gaponenko I.N., Ageev S.V., Iurev G.O., Shemchuk O.S., Meshcheriakov A.A., Petrov A.V., Solovtsova I. L., Vasina L.V., Tennikova T.B., Murin I.V., Semenov K.N., Sharoyko V.V. // Toxicology in Vitro. 2020. Vol. 62. P. 104683. doi 10.1016/j.tiv.2019.104683
  31. 31. Galebskaya L.V., Solovtsova I.L., Miroshnikova E.B., Mikhailova I.A., Sushkin M.E., Razumny A.V., Babina A.V., Fomina V.A. // Biomed. Photonics. 2017. Vol. 6. N 3. P. 33. doi 10.24931/2413-9432-2017-6-3-33-38
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