Synthesis and Antioxidant Activity (4-(Benzo[d][1,3]-dioxol-6-yl)-tetrahydro-2H-pyran-4-yl)methylsubstituted Aryloxypropanolamines, Aminoamides and Sulfanilamides

Zh. S. Arustamyan; Арустамян Ж. С.; R. E. Margaryan; Маркарян Р. Э.; G. G. Mkryan; Мкрян Г. Г.; A. A. Aghekyan; Агекян А. А.; G. A. Panosyan; Паносян Г. А.; Zh. M. Buniatyan; Буниатян Ж. М.; R. E. Muradyan; Мурадян Р. Е.

doi:10.31857/S0514749224010072

Synthesis and Antioxidant Activity (4-(Benzo[d][1,3]-dioxol-6-yl)-tetrahydro-2H-pyran-4-yl)methylsubstituted Aryloxypropanolamines, Aminoamides and Sulfanilamides

Autores: Arustamyan Z.S.¹, Margaryan R.E.¹, Mkryan G.G.¹, Aghekyan A.A.¹, Panosyan G.A.¹, Buniatyan Z.M.¹, Muradyan R.E.¹
Afiliações:
1. The Scientific Technological Centre of Organic and Pharmaceutical Chemistry NAS RA
Edição: Volume 60, Nº 1 (2024)
Páginas: 86-93
Seção: Articles
URL: https://journals.rcsi.science/0514-7492/article/view/272384
DOI: https://doi.org/10.31857/S0514749224010072
EDN: https://elibrary.ru/ENFSQA
ID: 272384

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Alkylation of 3,4-methylenedioxyphenylacetоnitrile with 2,2-dichlorodiethyl ether gave the corresponding nitrile the reduction of which with lithium aluminum hydride isolated (4-(benzo[d][1,3]dioxol-6-yl)-tetrahydro-2H-pyran-4-yl)methylamine. The interaction of the latter with aryloxymethyloxiranes gave the corresponding 1-((4-(benzo[d][1,3]dioxol-6-yl)-tetrahydro-2H-pyran-4-yl)methylamino)-3-aryloxypropan-2-ols. By the reaction of the same amine with chloroacetyl chloride isolated chloroacetamide, the interaction of which with a variety of secondary amines and heterylthiols synthesized the corresponding substituted amino- and sulfanylacetamides - derivatives of (4-(benzo[d][1,3]dioxol-6-yl)-tetrahydro-2H-pyran-4-yl)methylamine. The antioxidant activity of the obtained compounds was studied.

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(4-(benzo[d][1,3]dioxol-6-yl)-tetrahydro-2H-pyran-4-yl)methylamine, aryloxyaminopropanol, aminoamide, sulfanilamide

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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., Borch M., Andreasen J.T., Andersen J., Balle T., Kristensen J.L. J. Med. Chem. 2013, 56 (23), 9673–9682. doi: 10.1021/jm4013592
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
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
Хушматов Ш.С., Жумаев И.З., Журакулов Ш.Н., Саидов А.Ш., Виноградова В.И. Хим.-фарм. ж. 2020, 54 (1), 9–13. [Khushmatov Sh.S., Zhumaev I.Z., Zhurakulov Sh.N., Saidov A.Sh., Vinogradova V.I. Pharm. Chem. J. 2020, 54 (1), 7–11.] doi: 10.1007/s11094-020-02148-4
Watanuki S., Matsuura K., Tomura Y., Okada M., Okazaki T., Ohta M., Tsukamoto S. Bioorg. Med. Chem. 2011, 19, 5628–5638. doi: 10.1016/j.bmc.2011.07.030
Агекян А.А., Мкрян Г.Г., Цатинян А.С., Норавян О.С., Гаспарян Г.В. ЖОрХ. 2016, 52 (2), 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
Kankanala J., Marchand Ch., Abdelmalak M., Aihara H., Pommier Y., Wang Z. J. Med. Chem. 2016, 59, 2734. doi: 10.1021/acs.jmedchem.5b01973
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
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 (14), 3913–3924. doi: 10.1016/j.bmc.2014.12.007
Агекян А.А., Мкрян Г.Г., Цатинян А.С., Норавян О.С., Гаспарян Г.В. ЖОрХ. 2017, 53 (3), 364–367. [Aghekyan A.A., Mkryan G.G., Tsatinyan A.S., Noravyan O.S., Gasparyan G.V. Russ. J. Org. Chem. 2017, 53 (3), 362–365.] doi: 10.1134/S1070428017030083
Арутюнян А.В., Дубинина Е.Е., Зыбина Н.А. Методы оценки свободнорадикального окисления и антиоксидантной системы организма. СПб, 2000, 90–94.
Владимиров Ю.А., Азизова О.А., Даев А.И., Козлов А.В. Свободные радикалы в живых системах. ВИНИТИ, 1991, 29, 126–130.