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Optimization of the Synthesis of New Antibacterial Compounds with Tris(1-Alkylindol-3-YL)Methylium Fragments

  • DRUG SYNTHESIS METHODS AND MANUFACTURING TECHNOLOGY
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Pharmaceutical Chemistry Journal Aims and scope

A new optimal synthetic scheme for new antibacterial compounds combining tris-(1-alkyindol-3-yl)methylium and 3-(indol-1-yl)maleimide in their structures was developed. The proposed method provided a significant increase in the product yield, reduced the labor intensiveness and number of steps, and used readily accessible starting reagents. Agood yield was achieved for 3-(formylindol-1-yl)-4-chloromaleimide, a universal precursor enabling two-step syntheses of target tri(indolyl)methanes and production of an extensive library of analogous potentially active compounds from other 1-alkylindoles and various amines and thiols.

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References

  1. L. J. Shallcross and S. C. Davies, J. Antimicrob. Chemother., 69(11), 2883 – 2885 (2014).

    Article  CAS  Google Scholar 

  2. C. A. Arias and M. D. Murray, N. Engl. J. Med., 360(5), 439 – 443 (2009).

    Article  CAS  Google Scholar 

  3. F. M. MacKenzie, M. J. Struelens, K. J. Towner, and I. M. Gould, Clin. Microbiol. Infect., 11(11), 938 – 954 (2005).

    Article  CAS  Google Scholar 

  4. L. A. Kayukova and E. A. Berikova, Pharm. Chem. J., 54(6), 555 – 563 (2020).

    Article  CAS  Google Scholar 

  5. S. N. Lavrenov, A. Yu. Simonov, A. A. Panov, et al., Antibiot. Khimioter., 63(7 – 8), 3 – 9 (2018).

    Google Scholar 

  6. E. V. Stepanova, A. A. Shtil, S. N. Lavrenov, et al., Russ. Chem. Bull., 59(12), 2259 – 2267 (2010).

    Article  CAS  Google Scholar 

  7. S. N. Lavrenov, Y. N. Luzikov, E. E. Bykov, et al., Bioorg. Med. Chem., 18, 6905 – 6913 (2010).

    Article  CAS  Google Scholar 

  8. S. N. Lavrenov, O. P. Bychkova, L. G. Dezhenkova, et al., Chem. Heterocycl. Compd., 56(6), 741 – 746 (2020).

    Article  CAS  Google Scholar 

  9. N. A. Durandin, V. B. Tsvetkov, E. E. Bykov, et al., J. Photochem. Photobiol., B, 162, 570 – 576 (2016).

    Article  CAS  Google Scholar 

  10. S. Soltani, N. Montazeri, M. M. Zeydi, et al., Pharm. Chem. J., 53(10), 947 – 952 (2020).

    Article  CAS  Google Scholar 

  11. S. Mahboobi, E. Eichhorn, A. Popp, et al., Eur. J. Med. Chem., 41, 176 – 191 (2006).

    Article  CAS  Google Scholar 

  12. A. Panov, S. Lavrenov, A. Simonov, et al., J. Antibiot., 72(2), 122 – 124 (2019).

    Article  CAS  Google Scholar 

  13. L. V. Ektova, V. A. Eremina, N. I. Tikhonova, et al., Pharm. Chem. J., 54(5), 455 – 458 (2020).

    Article  CAS  Google Scholar 

  14. A. A. Panov, A. Y. Simonov, S. N. Lavrenov, et al., Chem. Heterocycl. Compd., 54(2), 103 – 113 (2018).

    Article  CAS  Google Scholar 

  15. S. S. Efimova, T. E. Tertychnaya, S. N. Lavrenov, and O. S. Ostroumova, Acta Nat., 11(3), (42), 38 – 45 (2019).

  16. L. V. Ektova, O. V. Goryunova, V. A. Eremina, et al., Pharm. Chem. J., 53(7), 604 – 609 (2019).

    Article  CAS  Google Scholar 

  17. E. A. Kuznetsova, K. N. Kolyasnikova, A. K. Golubyatnikova, et al., Pharm. Chem. J., 54(6), 642 – 646 (2020).

    Article  CAS  Google Scholar 

  18. M. M. Faul, L. L. Winneroski., and C. A. Krumrich, Tetrahedron Lett., 40, 1109 (1999).

  19. S. A. Lakatosh, E. E. Bykov, and M. N. Preobrazhenskaya, Chem. Heterocycl. Compd., 46(10), 1224 – 1232 (2011).

    Article  CAS  Google Scholar 

  20. G.-Q. Xul, C. Zhang, L. Zhang, et al., Arch. Pharm. Chem. Life Sci., 341, 273 (2008).

    Article  Google Scholar 

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Acknowledgments

Thee work was supported by a Russian Science Foundation Grant (Project No. 16 – 15 – 10300P).

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Correspondence to A. Yu. Simonov.

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Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 54, No. 12, pp. 33 – 38, December, 2020.

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Simonov, A.Y., Panov, A.A., Trenin, A.S. et al. Optimization of the Synthesis of New Antibacterial Compounds with Tris(1-Alkylindol-3-YL)Methylium Fragments. Pharm Chem J 54, 1263–1268 (2021). https://doi.org/10.1007/s11094-021-02352-w

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  • DOI: https://doi.org/10.1007/s11094-021-02352-w

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