N’-(5H-Chromeno[2,3-b]pyridin-5-yl)-N-(cyclo)alkanoylhydrazines: Synthesis and Biological Activity

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription Access

Abstract

A series of N’-(5H-chromeno[2,3-b]pyridin-5-yl)-N-(cyclo)alkanoylhydrazines was prepared for the first time by the reaction of 5H-chromeno[2,3-b]pyridin-5-ol with (cyclo)alkanoylhydrazines in acetic acid medium and their antioxidant and antibacterial activities were investigated. Three alternative methods for the synthesis of N’-(5H-chromeno[2,3-b]pyridin-5-yl)-N-(cyclo)alkanoylhydrazines were proposed. The stability of the obtained compounds, depending on the structure of the hydrocarbon radical, their antioxidant and antibacterial activities were studied. The greatest antibacterial effect of N’-(5H-chromeno[2,3-b]pyridin-5-yl)-N-(cyclo)alkanoylhydrazines was shown against the mycomembrane bacteria Mycobacterium smegmatis me2 155.

About the authors

V. Yu Gorokhov

Institute of Technical Chemistry of the Ural Branch of the Russian Academy of Sciences

Author for correspondence.
Email: Gorokhov_V.Yu@mail.ru
ORCID iD: 0000-0003-3829-5038
branch of the Perm Federal Research Center of the Ural Branch of the Russian Academy of Sciences Perm, Russia

T. V Polyudova

Institute of Ecology and Genetics of Microorganisms of the Ural Branch of the Russian Academy of Sciences; Perm Agrarian-Technological University named after academician D.N. Pryanishnikov

Email: Gorokhov_V.Yu@mail.ru
ORCID iD: 0000-0003-2618-762X

branch of the Perm Federal Research Center of the Ural Branch of the Russian Academy of Sciences

Perm, Russia; Perm, Russia

S. A Zabolotnykh

Institute of Technical Chemistry of the Ural Branch of the Russian Academy of Sciences

Email: Gorokhov_V.Yu@mail.ru
ORCID iD: 0000-0001-8307-0386

branch of the Perm Federal Research Center of the Ural Branch of the Russian Academy of Sciences

Perm, Russia

S. M Gorokhova

Perm Agrarian-Technological University named after academician D.N. Pryanishnikov; Perm State National Research University

Email: Gorokhov_V.Yu@mail.ru
ORCID iD: 0000-0001-8609-0294
Perm, Russia; Perm, Russia

L. G Chekanova

Institute of Technical Chemistry of the Ural Branch of the Russian Academy of Sciences

Email: Gorokhov_V.Yu@mail.ru
ORCID iD: 0000-0003-1792-6945

branch of the Perm Federal Research Center of the Ural Branch of the Russian Academy of Sciences

Perm, Russia

References

  1. Oe T., Tsuruda M., Matsuo H., Sakuragi S., Terasawa M., Goto K. // Yakugaku Zasshi. 1983. Vol. 103. N 3. P. 300. doi: 10.1248/yakushi1947.109.11_827
  2. Bristol J.A., Gold E.H., Gross I., Lovey R.G. // J. Med. Chem. 1981. Vol. 24. N 8. P. 1010. doi: 10.1021/jjm00140a020
  3. Nifant’ev I.E., Besprozvannykh V.K., Shlyakhtin A.V., Tavtorkin A.N., Smirnova M.P., Levin I.S., Ivchenko P.V. // Mendeleev Commun. 2021. Vol. 31. N 3. P. 664. doi: 10.1016/j.mencom.2021.04.032
  4. Oliveira-Pinto S., Pontes O., Lopes D., Sampaio-Marques B., Costa M.D., Carvalho L., Gonçalves C.S., Costa B.M., Maciel P., Ludovico P., Baltazar F., Proença F., Costa M. // Bioorg. Chem. 2020. Vol. 100. P. 103942. doi: 10.1016/j.bioorg.2020.103942
  5. Halawa A.H., Elaasser M.M., El Kerdany A.M., Abd El-Hady A.M.A.I., Emam H.A., El-Agrody A.M. // Med. Chem. Res. 2017. Vol. 26. P. 2624. doi: 10.1007/s00044-017-1961-3
  6. Bizarro A., Sousa D., Lima R.T., Musso L., Cincinelli R., Zuco V., De Cesare M., Dallavalle S., Vasconcelos M.H. // Molecules. 2018. Vol. 23. N 2. P. 407. doi: 10.3390/molecules230204
  7. Hedidi M., Maillard J., Erb W., Lassagne F., Halauko Yu.S., Ivashkevich O.A., Matulis V.E., Roisnel T., Dorcet V., Hamze M., Fajloun Z., Baratte B., Ruchaud S., Bach S., Bentabed-Ababas G., Mongin F. // Eur. J. Org. Chem. 2017. Vol. 2017. N 31. P. 5903. doi: 10.1002/ejoc.201701004
  8. Kancheria R., Lohith T.N., Deshmukh S., Mukha S.R., Kuruvalli G., Reddy M.B.M. // Mol. Divers. 2024. doi: 10.1007/s11030-024-10982-x
  9. Ukawa K., Ishiguro T., Kuriki H., Nohara A. // Chem. Pharm. Bull. 1985. Vol. 33. N 10. P. 4432. doi: 10.1248/cpb.33.4432
  10. Dimitriadou E., Rafropoulou M., Kasapidou P.M., Tsoleridis C.A., Stephanidou-Stephanatou J., Hadji-pavlou-Litina D.J., Kontogiorgis C., Prissa A., Papadopoulos A. // Arkivoc. 2014. Vol. 2014. N 4. P. 372. doi: 10.3998/ark.5550190.p008.754
  11. Weinstein D.S., Gong H., Doweyko A.M., Cunningham M., Habe S., Wang J.H., Holloway D.A., Burke C., Gao L., Guarino V., Carman J., Somerville J.E., Shuster D., Salter-Cid L., Dodd J.H., Nadler S.G., Barrish J.C. // J. Med. Chem. 2011. Vol 54. N 20. P. 7318. doi: 10.1021/jm200879j
  12. Teleha C. Pat. US 005594001 (1997).
  13. Brown B. Pat. US 005750528A (1998).
  14. Yielzoleh F.M., Nikodfar K., Darbarzi M.S., Zahedi-Ta-brizi M. // J. Mol. Struct. 2025. Vol. 1321. Pt 3. 140012. doi: 10.1016/j.molstruc.2024.140012.
  15. Alizadeh A., Rostampoor A. // ChemistrySelect. 2024. Vol. 9. N 36. P. e202400290. doi: 10.1002/slet.202400290
  16. Mai A.M., Magdy A.I., Al-Shimaa B. // Synth. Commun. 2024. Vol. 54. N 18. P. 1523. doi: 10.1080/00397911.2024.2394833
  17. Sharon K.N., Padmaia P., Tarun M. Sumanth E., Reddy P.N. // Russ. J. Org. Chem. 2023. Vol. 59. N 3. P. 470. doi: 10.1134/S1070428023030156
  18. Abdel-Monem Y.K., El-Enein S.A.A., El-Sheikh-Amer M.M. // J. Mol. Struct. 2017. Vol. 1127. P. 386. doi: 10.1016/j.molstruc.2016.07.110
  19. Sreenivasulu R. Sujitha P., Jadav S.S., Ahsan M.J., Kumar C.G., Raju R.R. // Monatsh. Chem. 2017. Vol. 148. P. 305. doi: 10.1007/s00706-016-1750-6
  20. Durgesh R., Sreenivasulu R., Raju R.R. // J. Pharm. Res. 2018. Vol. 12. P. 42.; Manzano C.M., Bergamini F.R.G., Formiga A.L.B., Corbi P.P., Ruiz A.L.T.G., de Oliveira E.C.S., Lustri W.R., Ribeiro M.A. // J. Mol. Struct. 2020. Vol. 1154. P. 469. doi: 10.1016/j.molstruc.2020.127912
  21. Kumar D., Judge V., Narang R., Sangwan S., De Clercq E., Balzarini J., Narasimhan B. // Eur. J. Med. Chem. 2010. Vol. 45. N 7. P. 2806. doi: 10.1016/j.ejmech.2010.03.002
  22. Kumar P., Narasimhan B., Yogeeswari P., Sriram D. // Eur. J. Med. Chem. 2010. Vol. 45. N 12. P. 6085. doi: 10.1016/j.ejmech.2010.08.030
  23. Suzen S. // Curr. Drug Deliv. 2013. Vol. 10. N 1. P. 71. doi: 10.2174/1567201811310010013
  24. Gwaram N.S., Ali H.M., Abdulla M.A., Buckle M.J., Sukumaran S.D., Chung L.Y., Othman R., Alhadi A.A., Yehye W.A., Hadi A.H., Hassandarvish P., Khaledi H., Abdelwahab S.I. // Molecules. 2012. Vol. 17. N 3. P. 2408. doi: 10.3390/molecules17032408
  25. Nastasă C., Tiperciuc B., Dunn M., Benedec D., Oniga O. // Molecules. 2015. Vol. 20. N 9. P. 17325. doi: 10.3390/molecules200917325
  26. Luo L., Jia B.-Z., Wei X.-Q., Xiao Z.-L., Wang H., Sun Y.-M., Shen Y.-D., Lei H.-T., Xu Z.-L. // Sensors Actuat. (B). 2021. Vol. 332. P. 129561. doi: 10.1016/j.snb.2021.129561
  27. Moskalyk R.E., Chatten L.G. // Canad. J. Chem. 2011. Vol. 45. N 13. P. 1411. doi: 10.1139/v67-233
  28. He C.-X., Meng H., Zhang X., Cui H.-Q., Yin D.-L. // Chinese Chem. Lett. 2015. Vol. 26. N 8. P. 951. doi: 10.1016/j.celet.2015.03.027
  29. Gorokhov V.Yu., Kharitonova A.V., Zabolotnykh S.A., Chekanova L.G. // Russian Journal of Organic Chemistry. 2025. Vol. 61. N 1. P. 35. doi: 10.1134/S1070428024602048
  30. Min Z., Junfa W., Zhangjiu W. // Zhongguo Yiyao Gongye Zazhi. 2004. Vol. 35. N 5. P. 267.
  31. Mikhalev A.I., Konshin M.E. // Chem. Heterocycl. Compd. 1976. Vol. 12. P. 1022. doi: 10.1007/BF00480398

Supplementary files

Supplementary Files
Action
1. JATS XML
Download

Copyright (c) 2025 Russian Academy of Sciences

Согласие на обработку персональных данных

 

Используя сайт https://journals.rcsi.science, я (далее – «Пользователь» или «Субъект персональных данных») даю согласие на обработку персональных данных на этом сайте (текст Согласия) и на обработку персональных данных с помощью сервиса «Яндекс.Метрика» (текст Согласия).