Synthesis and Antioxidant Activity of Alkyl N-(9H-Thioxanthen-9-yl)(cyclo)alkylhydrazides

Capa

Citar

Texto integral

Acesso aberto Acesso aberto
Acesso é fechado Acesso está concedido
Acesso é fechado Acesso é pago ou somente para assinantes

Resumo

A series of new alkyl N-(9H-thioxanthen-9-yl)(cyclo)alkylhydrazides was obtained for the first time by the reaction of (cyclo)alkylhydrazides, 9H-thioxanthen-9-ol and pyridinium perchlorate in a pyridine medium. The antioxidant activity of alkyl N-(9H-thioxanthen-9-yl)(cyclo)alkylhydrazides was studied. The greatest antioxidant effect was revealed in linear and cyclic N-(9H-thioxanthen-9-yl)(cyclo)alkylhydrazides, the values of which are in the range of 0.72–0.88 from ascorbic acid. The presence of a branched radical in N-(9H-thioxanthen-9-yl)alkylhydrazides significantly reduces the antioxidant properties.

Texto integral

Acesso é fechado

Sobre autores

V. Gorokhov

Institute of Technical Chemistry of the Ural Branch of the Russian Academy of Sciences, Perm Federal Research Center of the Ural Branch of the Russian Academy of Sciences

Autor responsável pela correspondência
Email: Gorokhov_V.Yu@mail.ru
ORCID ID: 0000-0003-3829-5038
Rússia, Perm, 614013

S. Zabolotnykh

Institute of Technical Chemistry of the Ural Branch of the Russian Academy of Sciences, Perm Federal Research Center of the Ural Branch of the Russian Academy of Sciences

Email: Gorokhov_V.Yu@mail.ru
ORCID ID: 0000-0001-8307-0386
Rússia, Perm, 614013

A. Kharitonova

Institute of Technical Chemistry of the Ural Branch of the Russian Academy of Sciences, Perm Federal Research Center of the Ural Branch of the Russian Academy of Sciences

Email: Gorokhov_V.Yu@mail.ru
ORCID ID: 0000-0002-4791-5799
Rússia, Perm, 614013

L. Chekanova

Institute of Technical Chemistry of the Ural Branch of the Russian Academy of Sciences, Perm Federal Research Center of the Ural Branch of the Russian Academy of Sciences

Email: Gorokhov_V.Yu@mail.ru
ORCID ID: 0000-0003-1792-6945
Rússia, Perm, 614013

Bibliografia

  1. Vacca J. Pat. US 11957687 (2024).
  2. Pellicciari R., Moroni F., Noe C. Pat. WO 0208220 (2002).
  3. Curry K. Pat. WO 20070010556 (2006).
  4. Filippatos E., Papadaki-Valiraki A., Roussakis C., Verbist J.-F. // Arch. Pharm. 1993. Vol. 326. N 8. P. 454. doi: 10.1002/ardp.19933260805
  5. He C.-X., Meng H., Zhang X., Cui H.-Q., Yin D.-L. // CCLET. 2015. Vol. 26. N 8. P. 951. doi 10.1016/ j.cclet.2015.03.027
  6. Cardoso J., Freitas-Silva J., Durães F., Carvalho D.T., Gales L., Pinto M., Sousa E., Pinto E. // Antibiotics. 2022. Vol. 11. N 11. P. 1488. doi: 10.3390/antibiotics11111488
  7. El-Sakka I.A., Zeid I.F., Abdel-Bary H.M., Abdel-Mageed A.E.S. // Arch. Pharm. 1994. Vol. 327. N 3. P. 133. doi: 10.1002/ardp.19943270303
  8. Suzen S. // Current Drug Delivery. 2013. Vol. 10. N 1. P. 71. doi: 10.2174/1567201811310010013
  9. 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
  10. Nastasă C., Tiperciuc B., Duma M., Benedec D., Oniga O. // Molecules. 2015. Vol. 20. N 9. P. 17325. doi: 10.3390/molecules200917325
  11. 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
  12. 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
  13. Durgesh R., Sreenivasulu R., Raju R.R. // J. Pharm. Res. 2018. Vol. 12. P. 42.
  14. 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
  15. 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
  16. 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
  17. Shao X., Tian L., Wang Y. // Eur. J. Org. Chem. 2019. Vol. 2019. N 25. 4089. doi: 10.1002/ejoc.201900714
  18. Юнникова Л.П., Лихарева Ю.Е., Исляйкин М.К., Данилова Е.А. // ЖОрХ. 2020. Т. 56. N 5. С. 784; Yunnikova L.P., Likhareva Yu.E., Islyaykin M.K., Danilova E.A. // Russ. J. Org. Chem. 2020. Vol. 56. N 5. P. 829. doi: 10.1134/S1070428020050152
  19. Yamaguchi T., Yamamoto Y., Kinoshita D., Akiba K., Zhang Y., Reed C.A., Hashizume D., Iwasaki F. // J. Am. Chem. Soc. 2008. Vol. 130. N 22. P. 6894. doi: 10.1021/ja710423d
  20. Иванов Г.Е., Туров А.В., Корнилов М.Ю. // Укр. хим. ж. 1987. Т. 53. № 7. С. 746.
  21. Иванов Г.Е., Туров А.В., Павлюк П.В., Максимчук А.Н., Корнилов М.Ю. // Укр. хим. ж. 1983. Т. 49. № 2. С. 190.
  22. Харитонова А.В., Радушев А.В., Батуева Т.Д., Горбунов А.А., Чеканова Л.Г. // Хим. технол. 2015. Т. 16. № 2. С 92.
  23. Колодяжная О.O., Колодяжный О.И. // ЖОХ. 2011. Т. 81. Вып. 1. С. 208; Kolodyazhnaya O.O., Kolodyazhnyi O.I. // Russ. J. Gen. Chem. 2011. Vol. 81. P. 308. doi: 10.1134/s107036321102006x
  24. CrysAlisPro, Rigaku Oxford Diffraction. 2022. Version 1.171.42.74a.
  25. Sheldrick G.M. // Acta Crystallogr. (A). 2015. Vol. 71. P. 3. doi: 10.1107/S2053273314026370
  26. Sheldrick G.M. // Acta Crystallogr. (C). 2015. Vol. 71. Р. 3. doi: 10.1107/S2053229614024218
  27. Dolomanov O.V., Bourhis L.J., Gildea R.J., Howard J.A.K., Puschmann H. // J. Appl. Cryst. 2009. Vol. 42. N 2. P. 340. doi: 10.1107/S0021889808042726
  28. Berker K.I., Güçlü K., Tor I., Apak R. // Talanta. 2007. Vol. 72. N 3. P. 1159. doi: 10.1016/j.talanta.2007.01.019
  29. Булатов М.И., Калинкин И.П. Практическое руководство по фотометрическим методам анализа. Л.: Химия, 1986. 432 с.
  30. Цюпко Т.Г., Петракова И.С., Бриленок Н.С., Николаева Н.А., Чупрынина Д.А., Темердашев З.А., Вершинин В.И. // Аналитика и контроль. 2011. Т. 15. № 3. 290.

Arquivos suplementares

Arquivos suplementares
Ação
1. JATS XML
Baixar
2. Fig. 1. General view of the 4d compound molecule according to X-ray diffraction data, represented by thermal ellipsoids with a 30% probability.

Baixar (83KB)
Metadados
3. 2. Values of antioxidant activity of alkyl-N-(9H-thioxanthene-9-yl)(cyclo)alkylhydrazides 4a–K.

Baixar (37KB)
Metadados
4. 3. Spectra of the FRAP solution before and after the addition of ascorbic acid (AC) or compound 4j (l = 10 mm, background – water, CA = 2.5·10-3 mol/l, c4j = 10-3 mol/l).

Baixar (50KB)
Metadados
5. Scheme 1.

Baixar (49KB)
Metadados

Declaração de direitos autorais © Russian Academy of Sciences, 2025