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Acid-Catalyzed Heterocyclization of Trialkylnaphthazarin Thioglucosides in Angular Quinone-Carbohydrate Tetracycles

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Abstract

Tetracyclic naphthoquinone-carbohydrate conjugates with an angular-fused heterocycle were obtained for the first time by the intramolecular condensation of naphthazarin thioglucosides in a mixture of n-butanol and methanesulfonic acid under reflux. The competing reaction is hydrolysis of the thioglucosidic bond with formation of trialkylmercaptonaphthazarins.

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References

  1. Thomson, R.H. Naturally Occurring Quinones IV, Chapman & Hall; London, UK, 1997.

  2. Sanchez-Calvo, J.M., Barbero, G.R., Guerrera-Vasquez, G., Duran, A.G., Macias, M., Rodrıguez-Iglesias, M.A., Molinillo, J.M.G., and Macias, F.A., Med. Chem. Res., 2016, vol.25, p.1274.

    Article  CAS  Google Scholar 

  3. Mishchenko, N.P., Fedoreev, S.A., and Bagirova, V.L., Pharm. Chem. J., 2003, vol.37, p.48. doi https://doi.org/10.1023/A:1023659331010

    Article  CAS  Google Scholar 

  4. Asche, C., Mini Rev. Med. Chem., 2005, vol.5, p.449.

    Article  CAS  PubMed  Google Scholar 

  5. Wellington, K.W., RSC Adv., 2015, vol.5, p.20309.

    Article  CAS  Google Scholar 

  6. Klotz, L., Hou, X., and Jacob, C., Molecules, 2014, vol.19, p.14902.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. Constantino, L. and Barlocco, D., Curr. Med. Chem., 2006, vol.13, p.65.

    Article  Google Scholar 

  8. Polonik, S.G., Prokof’eva, N.G., Agafonova, I.G., and Uvarova, N.I., Pharm. Chem. J., 2003, vol.37, p.397. doi https://doi.org/10.1023/A:1027305110622

    Article  CAS  Google Scholar 

  9. Su, Y., Xie, J., Wang, Y., Hub, X., and Lin, X., Eur. J. Med. Chem., 2010, vol.45, p.2713.

    Article  CAS  PubMed  Google Scholar 

  10. Pelageev, D.N., Dyshlovoy, S.A., Pokhilo, N.D., Denisenko, V.A., Borisova, K.L., Von Amsberg, G.K., Bokemeyer, C., Fedorov, S.N., Honecker, F., and Anufriev, V.Ph., Eur. J. Med. Chem., 2014, vol.77, p.139.

    Article  CAS  PubMed  Google Scholar 

  11. Lin, H.-Y., Han, H.-W., Bai, L.-F., Qiu, H.-Y., De-Zheng, Y., Qi, J.-L., Wang, X.-M., Gu, H.-W., and Yang, Y.-H., RSC. Adv., 2014, vol.4, p.49796. doi https://doi.org/10.1039/C4RA08810G

    Article  CAS  Google Scholar 

  12. Polonik, S.G., Tolkach, A.M., and Uvarova, N.I., Russ. Chem. Bull., 1996, vol.45, p.459. doi https://doi.org/10.1007/BF01433995

    Article  Google Scholar 

  13. Sabutskii, Y.E., Denisenko, V.A., Popov, R.S., and Polonik, S.G., Arkivoc, 2017, vol.iii, p.302. doi https://doi.org/10.24820/ark.5550190.p010.241

    Article  CAS  Google Scholar 

  14. Polonik, S.G. and Denisenko, V.A., Russ. Chem. Bull., 2009, vol.58, p.1062. doi https://doi.org/10.1007/s11172-009-0135-y

    Article  CAS  Google Scholar 

  15. Fedorov, S.N., Shubina, L.K., Kuzmich, A.S., and Polonik, S.G., Open Glycosci., 2011, vol.4, p.1.

    Article  CAS  Google Scholar 

  16. Huot R. and Brassard, P., Can. J. Chem., 1974, vol.54, p.838.

    Article  Google Scholar 

  17. Polonik, N.S., Polonik, S.G., Denisenko, V.A., Moiseenko, O.P., and Anufriev, V.Ph., Russ. J. Org. Chem., 2011, vol.47, p.1045. doi https://doi.org/10.1134/S1070428011070128

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Elyakov Pacific Institute of Bioorganic Chemistry, FEB RAS, pr. 100 let Vladivostoku 159, Vladivostok, 690022, Russia

    Y. E. Sabutskii, V. A. Denisenko, R. S. Popov & S. G. Polonik

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  1. Y. E. Sabutskii
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  2. V. A. Denisenko
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  3. R. S. Popov
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  4. S. G. Polonik
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Correspondence to S. G. Polonik.

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Russian Text © Y.E. Sabutskii, V.A. Denisenko, R.S. Popov, S.G. Polonik, 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 2, pp. 192–197.

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Sabutskii, Y.E., Denisenko, V.A., Popov, R.S. et al. Acid-Catalyzed Heterocyclization of Trialkylnaphthazarin Thioglucosides in Angular Quinone-Carbohydrate Tetracycles. Russ J Org Chem 55, 147–151 (2019). https://doi.org/10.1134/S1070428019020040

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  • DOI: https://doi.org/10.1134/S1070428019020040

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