Synthesis and biological activity of 4-fluorophenylcyclohexyl(tetrahydropyranyl)methyl-substituted aryloxypropanolamines

Cover Page

Cite item

Full Text

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

Abstract

By alkylation of 4-fluorophenylacetonitrile with dibrompеntane and 2.2-dichlor-diethylether the corresponding nitriles were obtained, with which reduction by lithium aluminium hydride [1-(4-fluorophenyl)cyclohexyl]- and [1-(4-fluorophenyl)tetrahydro-2 H -pyran-4-yl]methanamines were isolated. By the reaction of the latters with substituted in aromatic cycles aryloxymethyloxiranes new aryloxypropanolamines were been synthesized. Some of them by the action of formaline were transformed to the corresponding oxazolidines.

About the authors

A. A Aghekyan

The Scientific Technological Centre of Organic and Pharmaceutical Chemistry NAS RA

Email: aaghekyan@mail.ru

G. G Mkryan

The Scientific Technological Centre of Organic and Pharmaceutical Chemistry NAS RA

Email: aaghekyan@mail.ru

G. S Melikyan

Yerevan State University

Email: aaghekyan@mail.ru

H. A Panosyan

The Scientific Technological Centre of Organic and Pharmaceutical Chemistry NAS RA

Email: aaghekyan@mail.ru

A. S Tsatinyan

The Scientific Technological Centre of Organic and Pharmaceutical Chemistry NAS RA

Email: aaghekyan@mail.ru

A. S Grigoryan

The Scientific Technological Centre of Organic and Pharmaceutical Chemistry NAS RA

Email: aaghekyan@mail.ru

H. V Gasparyan

The Scientific Technological Centre of Organic and Pharmaceutical Chemistry NAS RA

Email: aaghekyan@mail.ru

References

  1. Yuzhakov S.D., Glushkov R.G., Mashkovskii M.D. J. Pharm. Chem. 1991, 25, 283-295. doi: 10.1007/bf00772116
  2. Сидоренко Б.А., Преображенский Д.В. бета-Адреноблокаторы. М.: Информатик, 1996.
  3. Satyanarayana M., Tiwari P., Triphati B.K., Srivastava A., Pratap R.J. Bioorg. Med. Chem. 2004, 12, 883-889. doi: 10.1016/j.bmc.2003.12.026
  4. Машковский М.Д. Лекарственные средства. М.: Новая волна, 2010, 262-278.
  5. Bonini C., Chiummiento L., Di Blasio N., Funicello M., Lupattelli P., Tramutola F., Berti F., Ostric A., Miertus S., Frecer V., Kong D.-X. J. Bioorg. Med. Chem. 2014, 22, 4792-4802. doi: 10.1016/j.bmc.2014.06.055
  6. Sun Q.-Y, Zhang W.-N., Xu J.-M., Cao Y.-B., Wu Q.-Y., Zhang D.-Z., Liu Ch.-M., Yu Sh.-Ch., Jiang Y.-Y. J. Eur. Med. Chem. 2007, 42, 1151-1157. doi: 10.1016/j.ejmech.2006.11.003
  7. O'Reilly М., Kirkwood N.K., Kenyon E.J., Huckvale R., Cantillon D.M., Waddell S.J., Ward S.E., Richardson G.P., Kros C.J., Derudas M. J. Med. Chem. 2019, 62, 5312-5329. doi: 10.1021/acs.jmedchem.8b01325
  8. Gupta Y., Kumar S., Zak S.E., Jones K.A., Upadhyay C., Sharma N., Azizi S.-A., Kathayat R.S., Herbert A.S., Durvasula R., Dickinson B.C., Dye J.M., Rathi B., Kempaiah P. J. Bioorg. Med. Chem. 2021, 47, 116393. doi: 10.1016/j.bmc.2021.116393
  9. Агекян А.А., Мкрян Г.Г., Гукасян Т.Г., Цатинян А.С., Ширинян Э.А., Асатран Т.О., Маркарян К.Ж., Григорян А.В., Маркарян Э.А. Хим. ж. Арм. 2010, 63, 398-403.
  10. Агекян А.А., Мкрян Г.Г., Цатинян А.С., Норавян О.С., Гаспарян Г.В. ЖОрХ. 2016, 52, 226-230.
  11. Aghekyan A.A., Mkryan G.G., Tsatinyan A.S., Noravyan O.S., Gasparyan G.V. Russ. J. Org. Chem. 2016, 52, 209-213. doi: 10.1134/s1070428016020081
  12. Inagaki H., Miyauchi S., Miyauchi R.N., Kawato H.C., Ohki H., Matsuhashi N., Kawakami K., Takahashi H., Takemura M. J. Med. Chem. 2003, 46, 1005-1015. doi: 10.1021/jm020328y
  13. Vаn de Water А., Janssens W., Van Neuten J., Xhonneux R., De Gree J., Verahegen H., Reneman R., Janssen P.A. J. Card. Pharmacol. 1988, 11, 552-563. doi: 10.1097/00005344-198805000-00007
  14. Watanuki S., Matsuura K., Tomura Y., Okada M., Okazaki T., Ohta M., Tsukamoto S. J. Bioorg. Med. Chem. 2011, 19, 5628-5638. doi: 10.1016/j.bmc.2011.07.030
  15. Lacivita E., Schepetkin I.A., Stama M.L., Kirpotina L.N., Colabufo N.A., Perrone R., Khlebnikov A.I., Quinn M.T., Leopoldo M. J. Bioorg. Med. Chem. 2015, 23, 3913-3924. doi: 10.1016/j.bmc.2014.12.007
  16. Авакян О.М. Симпато-адреналовая система. M.: Наука, 1977.
  17. Горкин В.З. Методы, основанные на измерении освобождаемого аммиака. М.: Медицина, 1981.

Copyright (c) 2023 Russian Academy of Sciences

This website uses cookies

You consent to our cookies if you continue to use our website.

About Cookies