Synthesis of new condensed pyrano[4,3-b]pyridines based on ethyl-3-aminopyrano[4,3-b]thieno[3,2-e]pyridine2-carboxylate derivative

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Abstract

Methods for the synthesis of new fused pyrano[4,3- b ]pyridine derivatives based on the ethyl-3-amino-pyrano[4,3- b ]thieno[3,2- e ]pyridine-2-carboxylate derivative have been developed. The interaction reactions of the condensed 3-(phenoxycarbonyl)-amino derivative with primary and secondary amines have been studied. It has been established that in the case of primary amines, the reaction is accompanied by cyclization with the formation of fused pyrimidines. However, when secondary amines are used, the structure of the final product depends on the reaction conditions. The antibacterial properties of the synthesized compounds were studied.

About the authors

V. V Dabaeva

Scientific and Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Science of the Republic of Armenia

Email: valyа.dabayeva@mail.ru

M. R Bagdasaryan

Scientific and Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Science of the Republic of Armenia

Email: valyа.dabayeva@mail.ru

E. G Paronikyan

Scientific and Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Science of the Republic of Armenia

Email: valyа.dabayeva@mail.ru

I. M Barkhudaryants

Scientific and Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Science of the Republic of Armenia

Email: valyа.dabayeva@mail.ru

G. A Panosyan

Scientific and Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Science of the Republic of Armenia

Email: valyа.dabayeva@mail.ru

G. M Stepanyan

Scientific and Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Science of the Republic of Armenia

Email: valyа.dabayeva@mail.ru

Sh. Sh. Dashyan

Scientific and Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Science of the Republic of Armenia

Email: valyа.dabayeva@mail.ru

References

  1. McBrien K.D., Gao Q., Huang S., Klohr S.E., Wang R.R., Pirnik D.M., Neddermann K.M., Bursuker I., Kadow K.F., Leet J.E. J. Nat. Prod. 1996, 59, 1151-1153. doi: 10.1021/np960521t
  2. Di Liberto M.G., Caldo A.J., Quiroga A.D., Riveira M.J., Derita M.G. ACS Omega. 2020, 5, 7481-7487. doi: 10.1021/acsomega.0c00225
  3. Upadhyay K.D., Dodia N.M., Khunt R.C., Chaniara R.S., Shah A.K. ACS Med. Chem. Lett. 2018, 9, 283-288. doi: 10.1021/acsmedchemlett.7b00545
  4. Nguyen S.T., Kwasny S.M., Ding X., Cardinale S.C., McCarthy C.T., Kim H.-S., Nikaido H., Peet N.P., Williams J.D., Bowlin T.L., Opperman T.J. Bioorg. Med. Chem. 2015, 23, 2024-2034. doi: 10.1016/j.bmc.2015.03.016
  5. Pham H.-T., Martin J.P., Le T.-G. Synth. Comm. 2020, 50, 1845-1853. doi: 10.1080/00397911.2020.175771
  6. Paronikyan E.G., Petrou A., Fesatidou M., Geronikaki A., Dashyan Sh.Sh., Mamyan S.S., Paronikyan R.G., Nazaryan I.M., Hakopyan H.H. Med. Chem. Commun. 2019, 1399-1411. doi: 10.1039/c9md00187e
  7. Дабаева В.В., Пилосян С.Г., Норавян А.С., Багдасарян М.Р., Григорян Г.Х., Алексанян Р.А. Хим.-фарм. ж. 2012, 42, 11-12.
  8. Dabaeva V.V., Pilosyan S.G., Noravyan A.S., Bagdasaryan M.R., Grigoryan G.Kh., Aleksanyan R.A. Pharm. Chem. J. 2008, 42, 668-669. doi: 10.1007/s11094-009-0218-y
  9. Дабаева В.В., Багдасарян М.Р., Норавян А.С., Казарян Ж.В., Джагацпанян И.А., Назарян И.М., Акопян А.Г. Хим.-фарм. ж. 2015, 49, 34-37.
  10. Dabaeva V.V., Bagdasaryan M.R., Noravyan A.S., Kazaryan Zh.V., Dzhagatspanyan I.A., Nazaryan I.M., Akopyan A.G. Pharm. Chem. J. 2016, 42, 830-8339. doi: 10.1007/s11094-016-1381-6
  11. Дабаева В.В., Багдасарян М.Р., Дашян Ш.Ш., Назарян И.М., Акопян А.Г., Пароникян Р.Г. Хим.-фарм. ж. 2018, 52, 28-33.
  12. Dabaeva V.V., Bagdasaryan M.R., Dashyan Sh.Sh., Dzhagatspanyan I.A., Nazaryan I.M., Akopyan A.G., Paronikyan R.G. Pharm. Chem. J. 2018, 52, 844-849. doi: 10.1007/s11094-019-1912-z
  13. Дабаева В.В., Багдасарян М.Р., Пароникян Е.Г., Тамазян Р.А., Айвазян А.Г., Дашян Ш.Ш. ЖОХ. 2019, 89, 1811-1816.
  14. Dabaeva V.V., Bagdasaryan M.R., Paronikyan E.G., Tamazyan R.A., Ayvazyan A.G., Dashyan Sh.Sh. Russ. J. Gen. Chem. 2019, 89, 2364-2368. doi: 10.1134/S1070363219060124
  15. Руководство по проведению доклинических исследований лекарственных средств. Ред. Миронов А.Н. М.: Медицина, 2012, 1.

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