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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Resumo

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.

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Sobre autores

R. Margaryan

The Scientific Technological Centre of Organic and Pharmaceutical Chemistry NAS RA

Email: aaghekyan@mail.ru
ORCID ID: 0000-0002-5066-0870
Armênia, prosp. Azatutyana, 26, Yerevan, 0014

G. Stepanyan

The Scientific Technological Centre of Organic and Pharmaceutical Chemistry NAS RA

Email: aaghekyan@mail.ru
ORCID ID: 0009-0006-6649-4439
Armênia, prosp. Azatutyana, 26, Yerevan, 0014

A. Aghekyan

The Scientific Technological Centre of Organic and Pharmaceutical Chemistry NAS RA

Autor responsável pela correspondência
Email: aaghekyan@mail.ru
ORCID ID: 0000-0001-6151-4951
Armênia, prosp. Azatutyana, 26, Yerevan, 0014

H. Panosyan

The Scientific Technological Centre of Organic and Pharmaceutical Chemistry NAS RA

Email: aaghekyan@mail.ru
ORCID ID: 0000-0001-8311-6276
Armênia, prosp. Azatutyana, 26, Yerevan, 0014

S. Arutyunyan

The Scientific Technological Centre of Organic and Pharmaceutical Chemistry NAS RA

Email: aaghekyan@mail.ru
ORCID ID: 0000-0003-3748-6975
Armênia, prosp. Azatutyana, 26, Yerevan, 0014

A. Tsatinyan

The Scientific Technological Centre of Organic and Pharmaceutical Chemistry NAS RA

Email: aaghekyan@mail.ru
ORCID ID: 0000-0002-0923-2380
Armênia, prosp. Azatutyana, 26, Yerevan, 0014

M. Grigoryan

The Scientific Technological Centre of Organic and Pharmaceutical Chemistry NAS RA

Email: aaghekyan@mail.ru
ORCID ID: 0000-0002-6705-8536
Armênia, prosp. Azatutyana, 26, Yerevan, 0014

G. Mkryan

The Scientific Technological Centre of Organic and Pharmaceutical Chemistry NAS RA

Email: aaghekyan@mail.ru
ORCID ID: 0000-0001-9879-9524
Armênia, prosp. Azatutyana, 26, Yerevan, 0014

Bibliografia

  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., Moskvina 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., Клецкий М.Е., Загребаев А.Д., Ткачук А.В., Курбатов С.В., Алешукина А.В., Голошва Е.В., Маркова 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., Tkachuk A.V., Kurbatov S.V., Aleshukina A.V., Goloshova 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., Гаспарян 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. [Arustamyan Zh.S., Markaryan R.E., Aghekyan A.A., Nazaryan I.M., Hakobyan A.G., Paronikyan R.G., Minasyan 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.
  18. https://rat-house@neurobotics.ru, Россия, Зеленоград.

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