Synthesis and antimicrobial activity of hexahydrochromeno[4,3-d]pyrimidine-2-thiones thiouronium salts

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Abstract

The thiouronium salts of chromeno[4,3- d ]pyrimidine-2-thiones were isolated as individual diastereomers and characterized by 1H, 13C NMR spectroscopy and mass spectrometry. Antibacterial and antifungal activity against sensitive strains of gram-negative bacteria E. coli and P. fluorescens , gram-positive bacteria S. aureus and fungi C. albicans was studied.

About the authors

E. S Makarova

Yaroslavl State Technical University

A. A Romanycheva

M.V. Dorogov Pharmaceutical Technologies Transfer Centre, K.D. Ushinsky Yaroslavl State Pedagogical University

M. V Blyumina

M.V. Dorogov Pharmaceutical Technologies Transfer Centre, K.D. Ushinsky Yaroslavl State Pedagogical University

A. A Shetnev

M.V. Dorogov Pharmaceutical Technologies Transfer Centre, K.D. Ushinsky Yaroslavl State Pedagogical University

S. I Filimonov

Yaroslavl State Technical University;M.V. Dorogov Pharmaceutical Technologies Transfer Centre, K.D. Ushinsky Yaroslavl State Pedagogical University

Email: filimonovsi@ystu.ru

References

  1. Ronchetti R., Moroni G., Carotti A., Gioiello A., Camaioni E. // RSC Med. Chem. 2021. Vol. 12. N 7. P. 1046. doi: 10.1039/d1md00058f
  2. Al-Masoudi N.A., Saleh B.A., Karim N.A., Issa A.Y., Pannecouque C. // Heteroatom Chem. 2011. Vol. 22. N 1. P. 44. doi: 10.1002/hc.20654
  3. El-Gohary N.S., Shaaban M.I. // Eur. J. Med. Chem. 2013. Vol. 63. P. 185. doi: 10.1016/j.ejmech.2013.02.010
  4. Davis I.D., Martin A.J., Stockler M.R. et al. // N. Engl. J. Med. 2019. Vol. 381. N 2. P. 121. doi: 10.1056/NEJMoa1903835
  5. Dandia A., Jain A.K. // J. Heterocycl. Chem. 2013. Vol. 50. N 1. P. 104. doi: 10.1002/jhet.1002
  6. Van Daele I., Munier-Lehmann H., Hendrickx P.M., Marchal G., Chavarot P., Froeyen M., Qing L., Martins J.C., Van Calenbergh S. // ChemMedChem. 2006. Vol. 1. N 10. P. 1081. doi: 10.1002/cmdc.200600028
  7. Kuzovlev A.S., Volkova D.A., Parfenova I.V., Kulakov I.V., Shkirdova A.O., Zamilatskov I.A., Chernyshev V.V., Rybakov V.B., Tyurin V.S., Fefilov N.N., Vasilchenko A.S. // New J. Chem. 2020. Vol. 44. N 19. P. 7865. doi: 10.1039/C9NJ05958J
  8. Маркосян А.И., Айвазян А.С., Габриелян С.А., Мамян С.С., Айвазян А.А., Аракелян А.Г. // ЖОХ. Т. 93. № 3. С. 363
  9. Markosyan A.I., Ayvazyan A.S., Gabrielyan S.H., Mamyan S.S., Ayvazyan A.A., Arakelyan H.H. // Russ. J. Gen. Chem. 2023. Vol. 93. N 3. P. 485. doi: 10.1134/S1070363223030040
  10. Raj V., Lee J.H., Shim J.J., Lee J. // J. Mol. Liq. 2022. Vol. 353. P.118775. doi: 10.1016/j.molliq.2022.118775
  11. Peng F., Liu T., Wang Q., Liu F., Cao X., Yang J., Liu L., Xie C., Xue W. // J. Agric. Food Chem. 2021. Vol. 69. N 37. P. 11085. doi: 10.1021/acs.jafc.1c03755
  12. Hashim J., Arshad N., Khan I., Nisar S., Ali B., Choudhary M.I. // Tetrahedron. 2014. Vol. 70. N 45. P. 8582. doi: 10.1016/j.tet.2014.09.069
  13. Barbosa F.A., Siminski T., Canto R.F., Almeida G.M., Mota N.S., Ourique F., Pedrosa R.C., Braga A.L. // Eur. J. Med. Chem. 2018. Vol. 155. P. 503. doi: 10.1016/j.ejmech.2018.06.026
  14. Quan Z.J., Zhang Z., Wang J.K., Wang X.C., Liu Y.J., Ji P.Y. // Heteroatom Chem. 2008. Vol. 19. N 2. P. 149. doi: 10.1002/hc.20386
  15. Shelke A.V., Bhong B.Y., Karade N.N. // Tetrahedron Lett. 2013. Vol. 54. N 6. P. 600. doi: 10.1016/j.tetlet.2012.11.098
  16. Pan B., Huang R., Zheng L., Chen C., Han S., Qu D., Zhu M., Wei P. // Eur. J. Med. Chem. 2011. Vol. 46. N 3. P. 819. doi: 10.1016/j.ejmech.2010.12.014
  17. Mahgoub M.Y., Elmaghraby A.M., Harb A.E.A., Ferreira da Silva J.L., Justino G.C., Marques M.M. // Molecules. 2019. Vol. 24. N 12. P. 2306. doi: 10.3390/molecules24122306
  18. Filimonov S.I., Chirkova Z.V., Kabanova M.V., Makarova E.S., Shetnev A.A., Panova V.A., Suponitsky K.Y. // ChemistrySelect. 2019. Vol. 4. N 33. P. 9550. doi: 10.1002/slct.201901997
  19. Макарова Е.С., Кабанова М.В., Филимонов C.И., Шетнев А.А., Супоницкий К.Ю. // Изв. АН. Сер. хим. 2022. № 5. C. 1034
  20. Makarova E.S., Kabanova M.V., Filimonov S.., Shetnev A.A., Suponitsky K.Yu. // Russ. Chem. Bull. 2022. Vol. 71. N 5. P. 1034. doi: 10.1007/s11172-022-3505-3
  21. Filimonov D.A., Lagunin A.A., Gloriozova T.A., Rudik A.V., Druzhilovskii D.S., Pogodin P.V., Poroikov V.V. // Chem. Heterocycl. Compd. 2014. Vol. 50. N 3. P. 444. doi: 10.1007/s10593-014-1496-1.
  22. CLSI, Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically, Approved Standard, 9th ed., CLSI document M07-A9, Clinical and Laboratory Standards Institute, 950 West Valley Road, Suite 2500, Wayne, Pennsylvania 19087, USA, 2012.
  23. Михедров А.С., Байков С.В., Проскурина И.К., Шетнев А.А., Котов А.Д. // ЖОХ. Т. 89. № 10. С. 1572
  24. Mikherdov A.S., Baikov S.V., Proskurina I.K., Shetnev A.A., Kotov A.D. // Russ. J. Gen. Chem. 2019. Vol. 89. N 10. P. 2062. doi: 10.1134/s1070363219100128
  25. Тарасенко М.В., Преснухина С.И., Байков С.В., Шетнев А.А. // ЖОХ. Т. 90. № 9. С. 1349
  26. Tarasenko M.V., Presnukhina S.I., Shetnev A.A., Baikov S.V // Russ. J. Gen. Chem. 2020. Vol. 90. N 9. P. 1611. doi: 10.1134/S1070363220090042
  27. Определение чувствительности микроорганизмов к антибактериальным препаратам (МУК 4.2.1890-04) // Клин. микробиол. антимикроб. химиотер. 2004. Т. 6. № 4. С. 306.

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