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Synthesis and Antioxidant Properties of Novel Polycycles with Tetrahydroquinoline and Chromane Fragments

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Abstract

The three-component acid-catalyzed cyclocondensation of arylamines with cyclopentadiene and 6-benzyloxy/hydroxy-(2,5,7,8-tetramethylchroman-2-yl)acetaldehyde was used to synthesize novel cycloadducts containing chromane and cyclopentene/cyclopentane-fused tetrahydroquinoline fragments. The antioxidant activity of the novel compounds was studied using a kinetic model of the initiated oxidation of 1,4-dioxane.

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REFERENCES

  1. Kouznetsov, V., Palma, A., Ewert, C., and Varlamov, A., J. Heterocycl. Chem., 1998, vol. 35, p. 761. https://doi.org/10.1002/jhet.5570350402

    Article  CAS  Google Scholar 

  2. Ramesh, E., Manian, R.D.R.S., Raghunathan, R., Sainath, S., and Raghunathan, M., Bioorg. Med. Chem., 2009, vol. 17, p. 660. https://doi.org/10.1016/j.bmc.2008.11.058

    Article  CAS  PubMed  Google Scholar 

  3. Ding, C.Z., Hunt, J.T., Ricca, C., and Manne, V., Bioorg. Med. Chem. Lett., 2000, vol. 10, p. 273. https://doi.org/10.1016/S0960-894X(99)00686-1

    Article  CAS  PubMed  Google Scholar 

  4. Fotie, J., Kaiser, M., Delfín, D.A., Manley, J., Reid, C.S., Paris, J.-M., Wenzler, T., Maes, L., Mahasenan, K.V., Li, C., and Werbovetz, K.A., J. Med. Chem., 2010, vol. 53, p. 966. https://doi.org/10.1021/jm900723w

    Article  CAS  PubMed  Google Scholar 

  5. Sridharan, V., Suryavanshi, P.A., and Menéndez, J.C., Chem. Rev., 2011, vol. 111, p. 7157. https://doi.org/10.1021/cr100307m

    Article  CAS  PubMed  Google Scholar 

  6. Glushkov, V.A. and Tolstikov, A.G., Russ. Chem. Rev., 2008, vol. 77, p. 137. https://doi.org/10.1070/rc2008v077n02abeh003749

    Article  CAS  Google Scholar 

  7. Ghashghaei, O., Masdeu, C., Alonso, C., Palacios, F., and Lavilla, R., Drug Discov. Today, 2018, vol. 29, p. 71. https://doi.org/10.1016/j.ddtec.2018.08.004

    Article  Google Scholar 

  8. Hensley, K., Benaksas, E.J., Bolli, R., Comp, P., Grammas, P., Hamdheydari, L., Mou, S., Pye, Q.N., Stoddard, M.F., Wallis, G., Williamson, K.S., West, M., Wechter, W.J., and Floyd, R.A., Free Radical Bio Med., 2004, vol. 36, p. 1. https://doi.org/10.1016/j.freeradbiomed.2003.10.009

    Article  CAS  Google Scholar 

  9. Manfredini, S., Vertuani, S., Manfredi, B., Rossoni, G., Calviello, G., and Palozza, P., Bioorg. Med. Chem., 2000, vol. 8, p. 2791. https://doi.org/10.1016/S0968-0896(00)00205-4

    Article  CAS  PubMed  Google Scholar 

  10. Odinokov, V.N., Spivak, A.Yu., and Knyshenko, O.V., Russ. J. Bioorg. Chem., 2007, vol. 33, p. 359. https://doi.org/10.1134/S1068162007040012

    Article  CAS  Google Scholar 

  11. Tolstikov, A.G., Glushkov, V.A., Tarantin, A.V., Kazanbaeva, G.F., Shashkov, A.S., Suponitsky, K.Y., and Dembitsky, V.M., Heteroatom. Chem., 2005, vol. 16, p. 605. https://doi.org/10.1002/hc.20159

    Article  CAS  Google Scholar 

  12. Tolstikov, A.G., Savchenko, R.G., Lukina, E.S., Nedopekin, D.V., Limantceva, R.M., Khalilov, L.M., Mescheryakova, E.S., and Odinokov, V.N., Helv. Chim. Acta, 2014, vol. 97, p. 1317. https://doi.org/10.1002/hlca.201300456

    Article  CAS  Google Scholar 

  13. Fonseca, T., Gigante, B., Marques, M.M., Gilchrist, T.L., and De Clercq, E., Bioorg. Med. Chem., 2004, vol. 12, p. 103. https://doi.org/10.1016/j.bmc.2003.10.013

    Article  CAS  PubMed  Google Scholar 

  14. Wang, X.S., Yin, M.Y., Wang, S.L., Wang, W., and Li, Y.L., J. Heterocycl. Chem., 2012, vol. 49, p. 585. https://doi.org/10.1002/jhet.824

    Article  CAS  Google Scholar 

  15. Ken-ichi, S., Matsuda, T., Taka-aki, K., Yamada, K., Mizutani, T., Matsui, S., Fukuhara, K., and Miyata, N., Biol. Pharm. Bull., 2003, vol. 26, p. 448. https://doi.org/10.1248/bpb.26.448

    Article  Google Scholar 

  16. Tolstikov, A.G., Savchenko, R.G., Lukina, E.S., Nedopekin, D.V., and Odinokov, V.N., Russ. Chem. Bull., 2013, vol. 62, p. 203. https://doi.org/10.1002/chin.201417201

    Article  CAS  Google Scholar 

  17. Emanuel’, N.M., Okislenie etilbenzola (Ethylbenzene Oxidation), Moscow: Nauka, 1984.

  18. Yakupova, L.R., Safiullin, R.L., Khairullina, V.R., Gerchikov, A.Ya., and Baimuratova, G.R., Kinet. Catal., 2008, vol. 49, p. 366. https://doi.org/10.1134/S0023158408030075

    Article  CAS  Google Scholar 

  19. Denisov, E.T. and Azatyan, V.V., Ingibirovanie tsepnykh reaktsii (Chain Reaction Inhibition), Chernogolovka: IKhFCh, 1996.

  20. Khairullina, V.R. Gerchikov, A.Y., Safarova, A.B., Khalitova, R.R., Spivak, A.Yu., Shakurova, E.R., and Odinokov, V.N., Kinet. Catal., 2011, vol. 52, p. 186. https://doi.org/10.1134/S0023158411020091

    Article  CAS  Google Scholar 

  21. CrysAlis, PRO, (revision, 1.171.37.35) A.T.L., Yarnton, Oxfordshire, 2012.

  22. Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K., and Puschmann, H., J. Appl. Crystallogr., 2009, vol. 42, p. 339. https://doi.org/10.1107/S0021889808042726

    Article  CAS  Google Scholar 

  23. Sheldrick, G., Acta Crystallogr., Sect. A, 2011, vol. 64, p. 112. https://doi.org/10.1107/S0108767307043930

    Article  CAS  Google Scholar 

  24. Sheldrick, G., Acta Crystallogr., Sect. C, 2015, vol. 71, p. 3. https://doi.org/10.1107/S2053229614024218

    Article  CAS  Google Scholar 

  25. Macrae, C.F., Sovago, I., Cottrell, S.J., Galek, P.T.A., McCabe, P., Pidcock, E., Platings, M., Shields, G.P., Stevens, J.S., Towler, M., and Wood, P.A., J. Appl. Crystallogr., 2020, vol. 53, p. 226. https://doi.org/10.1107/s1600576719014092

    Article  CAS  PubMed  PubMed Central  Google Scholar 

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Funding

The work was financially supported by the Russian Foundation for Basic Research (project no. 20-03-00649). The work was fulfilled in part in the framework of the Federal program no. AAAA-A19-119022290012-3.

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Authors and Affiliations

  1. Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences (UFRC RAS), 450075, Ufa, Russia

    R. G. Savchenko, R. M. Limantseva, E. S. Meshcheryakova, A. G. Tolstikov & V. N. Odinokov

  2. Bashkir State University, 450076, Ufa, Russia

    I. V. Safarova & G. M. Sharipova

Authors
  1. R. G. Savchenko
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  2. R. M. Limantseva
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  3. I. V. Safarova
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  4. G. M. Sharipova
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  5. E. S. Meshcheryakova
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  6. A. G. Tolstikov
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  7. V. N. Odinokov
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Corresponding author

Correspondence to R. G. Savchenko.

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Savchenko, R.G., Limantseva, R.M., Safarova, I.V. et al. Synthesis and Antioxidant Properties of Novel Polycycles with Tetrahydroquinoline and Chromane Fragments. Russ J Org Chem 58, 226–235 (2022). https://doi.org/10.1134/S1070428022020105

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  • DOI: https://doi.org/10.1134/S1070428022020105

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