SYNTHESIS, SYMPATHOLYTIC AND ADRENOLYTIC ACTIVITY OF AMINOAMIDES AND AMINОESTERS ON THE BASE OF 1-(BENZO[D][1,3]DIOXOL-5-YL)-CYCLOPENTANE- AND 4-(BENZO[D][1,3]DIOXOL-5-YL)TETRAHYDRO- 2H-PYRANE-4-CARBOXYLIC ACIDS

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Abstract

By the reaction of 2-(benzo[d][1,3]dioxol-5-yl)acetonitrile with dibromobutane and 2,2'-dichlorodiethyl ether, nitriles of 1-(benzo[d][1,3]dioxol-5-yl)cyclopentane- and 4-(benzo[d][1,3]dioxol-5-yl)tetrahydro-2H-pyran-4-carboxylic acids were synthesized, converted into the corresponding acids by alkaline hydrolysis. Targeted (benzo[d][1,3]dioxol-5-yl)cyclopentane(tetrahydropyran)-carboxamides and (benzo[d][1,3]dioxol-5-yl)cyclopentane(tetrahydropyran)-carboxylates were synthesized by interaction of acid chlorides of isolated acids with N,N-dialkylaminoalkyl- and heterylalkylamines, as well as with N,N-dialkylaminoalkyl- and heterylalkylalcohols. The effect of the synthesized compounds on the cardiovascular system and blood hemodynamics was studied.

About the authors

R. E. Margaryan

The Scientific Technological Centre of Organic and Pharmaceutical Chemistry NAS RA

prosp. Azatutyana, 26, Yerevan, 0014 Armenia

G. V. Stepanyan

The Scientific Technological Centre of Organic and Pharmaceutical Chemistry NAS RA

prosp. Azatutyana, 26, Yerevan, 0014 Armenia

A. A. Aghekyan

The Scientific Technological Centre of Organic and Pharmaceutical Chemistry NAS RA

Email: aaghekyan@mail.ru
prosp. Azatutyana, 26, Yerevan, 0014 Armenia

H. A. Panosyan

The Scientific Technological Centre of Organic and Pharmaceutical Chemistry NAS RA

prosp. Azatutyana, 26, Yerevan, 0014 Armenia

S. A. Arutyunyan

The Scientific Technological Centre of Organic and Pharmaceutical Chemistry NAS RA

prosp. Azatutyana, 26, Yerevan, 0014 Armenia

A. S. Tsatinyan

The Scientific Technological Centre of Organic and Pharmaceutical Chemistry NAS RA

prosp. Azatutyana, 26, Yerevan, 0014 Armenia

M. S. Grigoryan

The Scientific Technological Centre of Organic and Pharmaceutical Chemistry NAS RA

prosp. Azatutyana, 26, Yerevan, 0014 Armenia

G. G. Mkryan

The Scientific Technological Centre of Organic and Pharmaceutical Chemistry NAS RA

prosp. Azatutyana, 26, Yerevan, 0014 Armenia

References

  1. Коноваленко А.С., Шаблыкин О.В., Броваретс В.С., Шаблыкина О.В., Москвина В.С., Козитский А.В. ХГС. 2020, 56 (8), 1021–1029. [Konovalenko A.S., Shablykin O.V., Brovarets V.S., Shablykina O.V., Moskvi- na V.S., Kozytskiy A.V. Chem. Heterocycl. Compd. 2020, 56 (8), 1021–1029.] doi: 10.1007/s10593-020-02769-3
  2. Hikichi Y. Jap. J. Phytopath. 1993, 59, 369–374. doi: 10.3186/jjphytopath.59.369
  3. Nagate T., Kurashige S., Mitsuhashi S. Antimicrob. Agents Chemother. 1980, 17, 203–208. doi: 10.1128/AAC.17.2.203
  4. сrestey F., Jensen A.A., Soerensen C., Magnus C.B., Andreasen J.T., Peters G.H. J., Kristensen J.L. J. Med. Chem. 2018, 61, 1719–1729. doi: 10.1021/acs.jmedchem.7601895
  5. Davies S.G., Fletcher A.M., Frost A.B., Kennedy M.S., Roberts P.M., Thomson J.E. Tetrahedron. 2016, 72, 2139. doi: 10.1016/j.tet.2016.03.008
  6. Bernard S., Kummerer N., Urgast D., Hack F., Ungelenk J., Frank A., Schollmeyer D., Dieter N. Synthesis. 2024, 56 (16), 2537–2548. doi: 10.1055/a-2328-2947
  7. Yan X., Zheng J., Li W-D.Z. Tetrahedron Lett. 2023, 132, 154826. doi: 10.1016/j.tetlet.2023.154826
  8. Попов А.A., Дряпак А.H., Буров О.Н., Клец- кий М.Е., Загребаев А.Д., Ткачук А.В., Курба- тов С.В., Алешукина А.В., Голошва Е.В., Марко- ва К.Г., Березинская И.С., Твердохлебова Т.И. ХГС. 2023, 59, 604–609. [Popov A.A., Dryapak A.N., Burov O.N., Kletskii M.E., Zagrebaev A.D., Tka- chuk A.V., Kurbatov S.V., Aleshukina A.V., Golosho- va E.V., Markova K.G., Berezinskaya I.S., Tverdokhlebova T.I. Chem. Hetероcycl. Compd. 2023, 59, 604–609.] doi: 10.1007/s10593-023-03239-2
  9. Lacivita E., Schepetkin I.A., Stama M.L., Kirpotina L.N., Colabufo N.A., Perrone R., Khlebnikov A.I., Quinn M.T., Leopoldo M. Bioorg. Med. Chem. 2015, 23, 3913–3924. doi: 10.1016/j.bmc.2014.12.007
  10. Marinovic M., Rimac H., Carvalho L.P., Rola C., Santana S., Pavic K., Prudencio M., Rajic Z. Bioorg. Med. Chem. 2023, 94, 117468. doi: 10.1016/j.bmc.2023.117468
  11. Mашковский М.Д. Лекарственные средства, М.: Новая волна. 2010.
  12. Агекян А.А., Мкрян Г.Г., Цатинян А.С., Нора-вян О.С., Гаспарян Г.В. ЖОрХ. 2016, 52, 226–230. [Aghekyan A.A., Mkryan G.G., Tsatinyan A.S., Noravyan O.S., Gasparyan G.V. Russ. J. Org. Chem. 2016, 52 (2), 209–213.] doi: 10.1134/S1070428016020081
  13. Aгекян A.A., Мкрян Г.Г., Цатинян A.С., Гаспа- рян Г.В. ЖОХ. 2019, 89, 812–816. [Aghekyan A.A., Mkryan G.G., Tsatinyan A.S., Gasparyan G.V., Russ.J. Gen. Chem. 2019, 89, 1051–1054.] doi: 10.1134/S107036321905027X
  14. Арустамян Ж.С., Маркарян Р.Э., Агекян А.А., Назарян И.М., Акобян А.Г., Пароникян Р.Г., Минасян Н.С. ЖОрХ, 2019, 55, 896–900. [Arusta- myan Zh.S., Markaryan R.E., Aghekyan A.A., Nazaryan I.M., Hakobyan A.G., Paronikyan R.G., Mina- syan N.S. Russ. J. Org. Chem. 2019, 55, 796–799.] doi: 10.1134/S1070428019060095
  15. Krohs W., Ther L., Vogel G. Pat. 1124485. Germany, C.A. 1962, 57, 9738g.
  16. Arustamyan Zh.S., Margaryan R.E., Mkryan G.G., Aghekyan A.A., Panosyan H.A., Buniatyan Zh.M., Muradyan R.E. Russ. J. Org. Chem. 2024, 60, 18–24. doi: 10.1134/S1070428024010032.
  17. Авакян О.М. Симпато-адреналовая система. M.: Наука, 1977. https://rat-house@neurobotics.ru, Россия, Зеленоград.

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