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
- Authors: Margaryan R.E.1, Stepanyan G.V.1, Aghekyan A.A.1, Panosyan H.A.1, Arutyunyan S.A.1, Tsatinyan A.S.1, Grigoryan M.S.1, Mkryan G.G.1
-
Affiliations:
- The Scientific Technological Centre of Organic and Pharmaceutical Chemistry NAS RA
- Issue: Vol 61, No 3 (2025)
- Pages: 293-301
- Section: ЭКСПЕРИМЕНТАЛЬНЫЕ СТАТЬИ
- URL: https://medjrf.com/0514-7492/article/view/687813
- DOI: https://doi.org/10.31857/S0514749225030095
- EDN: https://elibrary.ru/EUDZPA
- ID: 687813
Cite item
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.
Full Text

About the authors
R. E. Margaryan
The Scientific Technological Centre of Organic and Pharmaceutical Chemistry NAS RA
Email: aaghekyan@mail.ru
ORCID iD: 0000-0002-5066-0870
Armenia, prosp. Azatutyana, 26, Yerevan, 0014
G. V. Stepanyan
The Scientific Technological Centre of Organic and Pharmaceutical Chemistry NAS RA
Email: aaghekyan@mail.ru
ORCID iD: 0009-0006-6649-4439
Armenia, prosp. Azatutyana, 26, Yerevan, 0014
A. A. Aghekyan
The Scientific Technological Centre of Organic and Pharmaceutical Chemistry NAS RA
Author for correspondence.
Email: aaghekyan@mail.ru
ORCID iD: 0000-0001-6151-4951
Armenia, prosp. Azatutyana, 26, Yerevan, 0014
H. A. Panosyan
The Scientific Technological Centre of Organic and Pharmaceutical Chemistry NAS RA
Email: aaghekyan@mail.ru
ORCID iD: 0000-0001-8311-6276
Armenia, prosp. Azatutyana, 26, Yerevan, 0014
S. A. Arutyunyan
The Scientific Technological Centre of Organic and Pharmaceutical Chemistry NAS RA
Email: aaghekyan@mail.ru
ORCID iD: 0000-0003-3748-6975
Armenia, prosp. Azatutyana, 26, Yerevan, 0014
A. S. Tsatinyan
The Scientific Technological Centre of Organic and Pharmaceutical Chemistry NAS RA
Email: aaghekyan@mail.ru
ORCID iD: 0000-0002-0923-2380
Armenia, prosp. Azatutyana, 26, Yerevan, 0014
M. S. Grigoryan
The Scientific Technological Centre of Organic and Pharmaceutical Chemistry NAS RA
Email: aaghekyan@mail.ru
ORCID iD: 0000-0002-6705-8536
Armenia, prosp. Azatutyana, 26, Yerevan, 0014
G. G. Mkryan
The Scientific Technological Centre of Organic and Pharmaceutical Chemistry NAS RA
Email: aaghekyan@mail.ru
ORCID iD: 0000-0001-9879-9524
Armenia, prosp. Azatutyana, 26, Yerevan, 0014
References
- 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
- Hikichi Y. Jap. J. Phytopath. 1993, 59, 369–374. doi: 10.3186/jjphytopath.59.369
- Nagate T., Kurashige S., Mitsuhashi S. Antimicrob. Agents Chemother. 1980, 17, 203–208. doi: 10.1128/AAC.17.2.203
- 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
- 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
- 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
- Yan X., Zheng J., Li W-D.Z. Tetrahedron Lett. 2023, 132, 154826. doi: 10.1016/j.tetlet.2023.154826
- 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
- 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
- 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
- Mашковский М.Д. Лекарственные средства, М.: Новая волна. 2010.
- 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
- 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
- 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
- Krohs W., Ther L., Vogel G. Pat. 1124485. Germany, C.A. 1962, 57, 9738g.
- 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.
- Авакян О.М. Симпато-адреналовая система. M.: Наука, 1977.
- https://rat-house@neurobotics.ru, Россия, Зеленоград.
Supplementary files
