UDC 547.793 UDC 547-313

SINTEZ, ANTIOKSIDANTNAYA AKTIVNOST' I SPEKTRAL'NAYA KHARAKTERISTIKA (E)-3-ARIL-5-(ARILEHTENIL)-1,2,4-OKSADIAZOLOV Sintez, antioksidantnaya aktivnost' i spektral'naya kharakteristika (E)-3-aril-5-(arilehtenil)-1,2,4-oksadiazolov

Published in From Chemistry Towards Technology Step-By-Step · Volume 7, Issue 3, 2026 · Pages 22–33 · Rubric: Scientific articles
DOI: https://doi.org/10.52957/2782-1900-2026-7-3-22-33
Received: 28.06.2026 Accepted: 20.08.2026 Published: 23.09.2026
Stat'ya posvyaschena sintezu i harakteristike 5-(alkenil)-3-aril-1,2,4-oksadiazolov. Shema sinteza vklyuchaet dve stadii: poluchenie trifenilfosfoniy hlorida i posleduyuschuyu ego kondensaciyu s al'degidami. Usovershenstvovany usloviya sinteza celevyh produktov putem zameny osnovaniya, chto pozvolilo uvelichit' ih vyhody i poluchit' ranee sinteticheski nedostupnye soedineniya. V spektrah YaMR ¹N produktov prisutstvuyut dublety, harakternye dlya protonov dvoynoy svyazi s konstantoy J=16,1-16,4 Gc, svidetel'stvuyuschie o E konfiguracii poluchennyh soedineniy. Obnaruzheny fluorescentnye i antioksidantnye svoystva dlya soedineniy, soderzhaschih elektronodonornye zamestiteli.
oksadiazol, olefin, reakciya Vittiga, antioksidantnaya aktivnosti
Funding
Issledovanie vypolneno pri finansovoy podderzhke Rossiyskogo nauchnogo fonda (proekt № 25-23-20245).
Text References
Text (RU) (PDF)
Read Download

1. Byrne P.A., Gilheany D.G. The modern interpretation of the Wittig reaction mechanism. Chem. Soc. Rev., 2013, 42(16), 6670-6696. DOI:https://doi.org/10.1039/c3cs60105f EDN: https://elibrary.ru/YBIFNC

2. Ryu H., Seo S., Cho S.-H., Kim H.S., Jung A., Kang D.W., Son K., Cui M., Hong S.-h., Sharma P.K., Choi S., Blumberg P.M., Frank-Foltyn R., Bahrenberg G., Stockhausen H., Schiene K., Christoph T., Frormann S., Lee J. 2-Alkyl/alkenyl substituted pyridine C-region analogues of 2-(3-fluoro-4-methylsulfonylaminophenyl)propanamides as highly potent TRPV1 antagonists. Bioorg. Med. Chem. Lett., 2014, 24(16), 4039-4043. DOI:https://doi.org/10.1016/j.bmcl.2014.05.074

3. Girgis A.S., Panda S.S., Srour A.M., Abdelnaser A., Nasr S., Moatasim Y., Kutkat O., El Taweel A., Kandeil A., Mostafa A., Ali M.A., Fawzy N.G., Bekheit M.S., Shalaby E.M., Gigli L., Fayad W., Soliman A.A.F. 3-Alkenyl-2-oxindoles: Synthesis, antiproliferative and antiviral properties against SARS CoV-2. Bioorg. Chem., 2021, 114, 105131. DOI:https://doi.org/10.1016/j.bioorg.2021.105131 EDN: https://elibrary.ru/WMQFOL

4. Varela M.T., Lima M.L., Galuppo M.K., Tempone A.G., de Oliveira A., Lago J.H.G., Fernandes J.P.S. New alkenyl derivative from Piper malacophyllum and analogues: Antiparasitic activity against Trypanosoma cruzi and Leishmania infantum. Chem. Biol. Drug Des., 2017, 90(5), 1007-1011. DOI:https://doi.org/10.1111/cbdd.12986

5. Wang J., Wu Y., Wang P. Modular and diverse synthesis of oxaheterocycles via Pd-catalyzed migratory 1,n cycloannulation of alkenes. Chem. Sci., 2025, 16, 20292-20299. DOI:https://doi.org/10.1039/d5sc06539a EDN: https://elibrary.ru/PPPAKW

6. Zhang Z., Li B., Liu Y., Li Y., Xiao Y., Wu H., Zhang Y. Synergistic In/amine-catalyzed cascade Michael Aldol reactions of alkenyl pyridines with diverse 1,4-dipoles. J. Org. Chem., 2025, 90(38), 13573-13588. DOI:https://doi.org/10.1021/acs.joc.5c01612 EDN: https://elibrary.ru/WTSIGY

7. Marshall C.M., Federice J.G., Bell C.N., Cox P.B., Njardarson J.T. An update on the nitrogen heterocycle compositions and properties of U.S. FDA-approved pharmaceuticals (2013–2023). J. Med. Chem., 2024, 67(14), 11622-11655. DOI:https://doi.org/10.1021/acs.jmedchem.4c00841 DOI: https://doi.org/10.1021/acs.jmedchem.4c01122; EDN: https://elibrary.ru/MKAHGH

8. Cherkasova A., Astolfi R., Nawrozkij M., Gladkikh B., Proia E., Giuliani L., Rotili D., Ragno R., Ivanov R. 1,2,4-Oxadiazoles in medicinal chemistry: trends of the last years. Eur. J. Med. Chem., 2025, 297, 117935. DOI:https://doi.org/10.1016/j.ejmech.2025.117935 EDN: https://elibrary.ru/VBAWBX

9. Avanzo R. E., Padrón J. M., D'Accorso N. B., Fascio M. L. Synthesis and in vitro antiproliferative activities of (5-aryl-1,2,4-oxadiazole-3-yl) methyl d-ribofuranosides. Bioorg. Med. Chem. Lett, 2017, 27, 3674–3677. DOI:https://doi.org/10.1016/j.bmcl.2017.07.015

10. Kulkarni R., Manjunatha K., Joy M. N. et al. Exploration of NMI-MsCl mediated amide bond formation for the synthesis of novel 3,5-substituted-1,2,4-oxadiazole derivatives: synthesis, evaluation of anti-inflammatory activity and molecular docking studies. Mol.Div., 2023, 27, 1867–1878. DOI:https://doi.org/10.1007/s11030-022-10536-z EDN: https://elibrary.ru/PNNCLU

11. Rangaswamy S., Sreenivasulu R., Babu V. R. et al. Design, synthesis, anticancer evaluation, and molecular docking studies of oxazole-incorporated naphthyridine derivatives. Chem. Biodivers, 2023, 20, e202300466. DOI:https://doi.org/10.1002/cbdv.202300466 EDN: https://elibrary.ru/LOUDXF

12. Steblecova I.A., Larin A.A., Fershtat L. L. Poslednie dostizheniya v sinteze farmakologicheski aktivnyh soedineniy-liderov na osnove 1,2,3-, 1,2,4- i 1,2,5-oksadiazolov. Uspehi himii, 2025, 94(10), 1-60 RCR5185. DOI:https://doi.org/10.59761/RCR5185 EDN: https://elibrary.ru/QHYJMZ

13. Varaprasadu B. D., Haridasyam S. B., Koppula S. K. Synthesis of novel pyrido[3,4-d] pyrimidine-thiazolidione-1,2,4-oxadiazoles as potent EGFR targeting anticancer agents. J. Heterocycl. Chem., 2024, 61(5), 789-798. DOI:https://doi.org/10.1002/jhet.4859 EDN: https://elibrary.ru/OQXGQB

14. Vasil’eva E.A., Alexeev M.A., Tarasenko M.V., Ivanovskiy S.A., Blumina M. V., Shetnev A.A. Wittig Olefination with Novel 1,2,4-Oxadiazole-Substituted Triphenylphosphonium Ylides. Russ J. Gen. Chem., 2026, 96, 162. DOI:https://doi.org/10.1134/S1070363225608075 EDN: https://elibrary.ru/TKFTHA

15. Yanovskaya L.A., Yufit S.S. Organicheskiy sintez v dvuhfaznyh sistemah. M.: Himiya, 1982, 184 s.

16. Mohamadi F., Still W. C. Dichlorocarbene cyclopropanation of allylic alcohols. Tetrahedron Lett.,1986, 27(8), 893-896. DOI:https://doi.org/10.1016/s0040-4039(00)84130-1

17. Fedorynski M., Ziolkowska W., Jonczyk A. Tetramethylammonium salts: highly selective catalysts for the preparation of gem-dichlorocyclopropanes from electrophilic alkenes and chloroform under phase-transfer catalysis conditions. J. Org. Chem., 1993, 58(22), 6120-6121. DOI:https://doi.org/10.1021/jo00074a047

18. Blois, M. Antioxidant Determinations by the Use of a Stable Free Radical. Nature, 1958, (181), 1199-1200. DOI:https://doi.org/10.1038/1811199a0

19. Yu L., Yang K., Yao L., Wang N., Kang H., Yao G., Li X., Qin B. Synthesis and Antifungal Activity of 1,2,4 Oxadiazole Derivatives. Molecules, 2025, 30(8), 1851. DOI:https://doi.org/10.3390/molecules30081851 EDN: https://elibrary.ru/EXYOXB

20. Kumar S., Wadhwa P. Synthesis, molecular docking and biological evaluation of 1,2,4-oxadiazole based novel non-steroidal derivatives against prostate cancer. Bioorg. Chem., 2024, 143, 107029. DOI:https://doi.org/10.1016/j.bioorg.2023.107029 EDN: https://elibrary.ru/VTFBUB