Synthesis and antifungal activity of new sulfides with fragments of metronidazole and monoterpenoids

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Abstract

The reaction of bromoacetylmetronidazole with monoterpene thiols of pinane and bornane structures yielded new sulfides, which were tested for antimicrobial activity and cytotoxicity. Compounds with fragments of myrtane and myrtentiols showed fungicidal activity against yeast fungi Candida albicans, Candida tropicalis and Candida parapsilosis, while derivatives with fragments of hydroxypinane thiols were not toxic to cells of the lung epithelium of the cow embryo.

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About the authors

S. N. Subbotina

Federal Research Center “Komi Scientific Center of the Ural Branch of the Russian Academy of Sciences”

Email: lezina-om@yandex.ru
ORCID iD: 0009-0001-0512-3478

Institute of Chemistry

Russian Federation, Syktyvkar, 167000

O. M. Lezina

Federal Research Center “Komi Scientific Center of the Ural Branch of the Russian Academy of Sciences”

Author for correspondence.
Email: lezina-om@yandex.ru
ORCID iD: 0000-0002-6105-5641

Institute of Chemistry

Russian Federation, Syktyvkar, 167000

O. N. Grebyonkina

Federal Research Center “Komi Scientific Center of the Ural Branch of the Russian Academy of Sciences”

Email: lezina-om@yandex.ru
ORCID iD: 0000-0002-1982-104X

Institute of Chemistry

Russian Federation, Syktyvkar, 167000

D. V. Sudarikov

Federal Research Center “Komi Scientific Center of the Ural Branch of the Russian Academy of Sciences”

Email: lezina-om@yandex.ru
ORCID iD: 0000-0001-5640-6956

Institute of Chemistry

Russian Federation, Syktyvkar, 167000

S. A. Lisovskaya

Kazan Scientific Research Institute of Epidemiology and Microbiology; Kazan State Medical University

Email: lezina-om@yandex.ru
ORCID iD: 0000-0002-4377-2567
Russian Federation, Kazan, 420015; Kazan, 420012

A. R. Kayumov

Kazan Federal University

Email: lezina-om@yandex.ru
ORCID iD: 0000-0001-7195-1557

Institute of Fundamental Medicine and Biology

Russian Federation, Kazan, 420008

S. A. Rubtsova

Federal Research Center “Komi Scientific Center of the Ural Branch of the Russian Academy of Sciences”

Email: lezina-om@yandex.ru
ORCID iD: 0000-0003-1224-8751

Institute of Chemistry

Russian Federation, Syktyvkar, 167000

References

  1. Celik A., Aras Ates N. // Drug Chem. Toxicol. 2006. Vol. 29. P. 85. doi: 10.1080/01480540500408663
  2. Upcroft J.A., Campbell R.W., Benakli K., Upcroft P., Vanelle P. // Antimicrob. Agents Chemother. 1999. Vol. 43. P. 73. doi: 10.1128/aac.43.1.73
  3. Patel O.P.S., Jesumoroti O.J., Legoabe L.J., Beteck R.M. // Eur. J. Med. Chem. 2021. Vol. 210. P. 112994. doi: 10.1016/j.ejmech.2020.112994
  4. Al-Masoudi N.A., Abbas Z.A.A. // Monatsh. Chem. 2015. Vol. 43. 147. P. 383. doi: 10.1007/s00706-015-1612-7
  5. Blanco Z., Mijares M.R., Ramirez H., Fernandez-Moreira E., Oviedo J.H, Rodriguez M.N., Charris J.E. // Parasitol. Res. 2021. Vol. 120. P. 3307. doi: 10.1007/s00436-021-07266-w
  6. Saadeh H.A., Mosleh I.M., Al-Bakri A.G., Mubarak M.S. // Monatsh. Chem. 2010. Vol. 141. P. 471. doi: 10.1007/s00706-010-0281-9
  7. Rodriguez M., Gutierrez J., Dominguez J., Peixoto P.A., Fernandez A., Rodriguez N., Deffieux D., Rojas L., Quideau S., Pouysegu L. // Arch. Pharm. 2020. Vol. 353. P. e2000002. doi: 10.1002/ardp.202000002
  8. Zhang X., Sangani C.B., Jia L.-X., Gong P.-X., Wang F., Wang J.-F., Zhu H.-L. // RSC Adv. 2014. Vol. 4. P. 54217. doi: 10.1039/c4ra08567a
  9. Alawadi D.Y., Saadeh H.A., Kaur H., Goyal K., Sehgal R., Ben Hadda T., ElSawy N.A., Mubarak M.S. // Med. Chem. Res. 2015. Vol. 24. P. 1196. doi: 10.1007/s00044-014-1197-4
  10. Bkhaitan M.M., Alarjah M., Mirza A.Z., Abdalla A.N., El-Said H.M., Faidah H.S. // Chem. Biol. Drug Des. 2018. Vol. 92. P. 1954. doi: 10.1111/cbdd.13366
  11. Nikitina L.E., Artemova N.P., Startseva V.A., Fedyunina I.V., Klochkov V.V. // Chem. Nat. Compd. 2017. Vol. 53. P. 5. doi: 10.1007/s10600-017-2131-z
  12. Baishya R., Nayak D.K., Karmakar S., Chattopadhyay S., Sachdeva S.S., Sarkar B.R., Ganguly S., Debnath M.C. // Chem. Biol. Drug. Des. 2014. Vol. 85. P. 504. doi: 10.1111/cbdd.12437
  13. Гребенкина О.Н., Лезина О.М., Изместьев Е.С., Фролова Л.Л., Рубцова С.А., Кучин А.В. // ЖОрХ. 2019. Т. 55. С. 1510; Grebyonkina O.N., Lezina O.M., Izmest’ev E.S., Frolova L.L., Rubtsova S.A., Kutchin A.V. // Russ. J. Org. Chem. 2019. Vol. 55. Р. 1469. doi: 10.1134/S0514749219100045
  14. Dungues G.J., Calas R., Deleris G. // J. Org. Chem. 1984. Vol. 49. P. 442. doi: 10.1021/jo00177a011
  15. Банина О.А., Судариков Д.В., Крымская Ю.В., Фролова Л.Л., Кучин А.В. // ХПС. 2015. Т. 2. С. 231; Banina O.A., Sudarikov D.V., Krymskaya Yu.V., Frolova L.L., Kutchin A.V. // Chem. Nat. Compd. 2015. Vol. 2. P. 261. doi: 10.1007/s10600-015-1257-0
  16. Martı́nez-Ramos F., Vargas-Dı́az M.E., Chacón-Garcı́a L., Tamariz J., Joseph-Nathan P., Zepeda L.G. // Tetrahedron Asym. 2001. Vol. 12. P. 3095. doi: 10.1016/S0957-4166(01)00545-6
  17. Изместьев Е.С., Судариков Д.В., Рубцова С.А., Слепухин П.А., Кучин А.В. // ЖОрХ. 2012. T. 48. C. 197; Izmest’ev E.S., Sudarikov D.V., Rubtsova S.A., Slepukhin P.A., Kuchin A.V. // Russ. J. Org. Chem. 2012. Vol. 48. P. 1407. doi: 10.1134/S1070428012110024
  18. Nаkano T., Shikisai Y., Okamoto Y. // Polym. J. 1996. Vol. 28. P. 51. doi: 10.1295/polymj.28.51
  19. Garipov M.R., Sabirova A.E., Pavelyev R.S., Shtyrlin N.V., Lisovskaya S.A., Bondar O.V., Laikov A.V., Romanova J.G., Bogachev M.I., Kayumov A.R., Shtyrlin Y.G. // Bioorg. Chem. 2020. Vol. 104. P. 104306. doi 10.1016/ j.bioorg.2020.104306
  20. Mosmann T. // J. Immunol. Methods. 1983. Vol. 65. P. 55. doi: 10.1016/0022-1759(83)90303-4

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