Advertisement

Russian Chemical Bulletin

, Volume 67, Issue 4, pp 731–742 | Cite as

Synthesis and biological activity of fluorine-containing amino derivatives based on 4-caranethiol

  • D. V. Sudarikov
  • Yu. V. Krymskaya
  • N. O. Il’chenko
  • P. A. Slepukhin
  • S. A. Rubtsova
  • A. V. Kutchin
Full Article
  • 24 Downloads

Abstract

Fluorine-containing N-substituted sulfinamides were synthesized via 4-caranethiol-based sulfenimines and sulfinimines. Stereochemical features of oxidation of sulfenimines and addition of fluorine-containing reagents to sulfinimines were discussed. Antimicrobial activities of the obtained compounds were screened.

Key words

4-caranethiol sulfenimines sulfinimines chiral fluorine-containing N-substituted α-branched sulfinamides Ruppert–Prakash reagent fluorine-containing Reformatsky reagent antimicrobial activity 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    V. A. Soloshonok, D. V. Avilov, V. P. Kukhar´, L. Van Meervelt, N. Mischenko, Tetrahedron Lett., 1997, 38, 4903.CrossRefGoogle Scholar
  2. 2.
    V. A. Soloshonok, V. P. Kukhar, Tetrahedron, 1997, 53, 8307.CrossRefGoogle Scholar
  3. 3.
    N. C. Yoder, K. Kumar, Chem. Soc. Rev., 2002, 31,335.CrossRefPubMedGoogle Scholar
  4. 4.
    X.-L. Qiu, W.-D. Meng, F.-L. Qing, Tetrahedron, 2004, 60, 6711.CrossRefGoogle Scholar
  5. 5.
    C. Isanbor, D. O´Hagan, J. Fluorine Chem., 2006, 127,303.CrossRefGoogle Scholar
  6. 6.
    W. K. Hagmann, J. Med. Chem., 2008, 51, 4359.CrossRefPubMedGoogle Scholar
  7. 7.
    R. I. Mathad, B. Jaun, O. Flögel, J. Gardiner, M. Löweneck, J. D. C. Codée, P. H. Seeberger, D. Seebach, M. K. Edmonds, F. H. M. Graichen, A. D. Abell, Helv. Chim. Acta, 2007, 90, 2251.CrossRefGoogle Scholar
  8. 8.
    D. Seebach, A. K. Beck, D. J. Bierbaum, Chem. Biodivers., 2004, 1, 1111.CrossRefPubMedGoogle Scholar
  9. 9.
    H. Pellissier, Tetrahedron, 2006, 62, 5559.CrossRefGoogle Scholar
  10. 10.
    P. Zhou, B.-C. Chen, F. A. Davis, Tetrahedron, 2004, 60, 8003.CrossRefGoogle Scholar
  11. 11.
    D. Morton, R. A. Stockman, Tetrahedron, 2006, 62, 8869.CrossRefGoogle Scholar
  12. 12.
    J. A. Ellman, T. D. Owens, T. P. Tang, Acc. Chem. Res., 2002, 35,984.CrossRefPubMedGoogle Scholar
  13. 13.
    P. Bravo, G. Cavicchio, M. Crucianelli, A. L. Markovsky, A. Volonterio, M. Zanda, Synlett, 1996,887.Google Scholar
  14. 14.
    S. Fustero, A. Navarro, B. Pina, J. G. Soler, A. Bartolomé, A. Asensio, A. Simón, P. Bravo, G. Fronza, A. Volonterio, M. Zanda, Org. Lett., 2001, 3, 2621.CrossRefPubMedGoogle Scholar
  15. 15.
    M. Crucianelli, N. Battista, P. Bravo, A. Volonterio, M. Zanda, Molecules, 2000, 5, 1251.CrossRefGoogle Scholar
  16. 16.
    G. Dutheuil, S. Couve-Bonnaire, X. Pannecoucke, Angew. Chem., Int. Ed., 2007, 46, 1290.CrossRefGoogle Scholar
  17. 17.
    P. Bravo, M. Crucianelli, B. Vergani, M. Zanda, Tetrahedron Lett., 1998, 39, 7771.CrossRefGoogle Scholar
  18. 18.
    A. Asensio, P. Bravo, M. Crucianelli, A. Farina, S. Fustero, J. G. Soler, S. V. Meille, W. Panzeri, F. Viani, A. Volonterio, M. Zanda, Eur. J. Org. Chem., 2001, 1449.Google Scholar
  19. 19.
    M. Crucianelli, F. D. Angelis, F. Lazzaro, L. Malpezzi, A. Volonterio, M. Zanda, J. Fluorine Chem., 2004, 125,573.CrossRefGoogle Scholar
  20. 20.
    V. L. Truong, M. S. Ménard, I. Dion, Org. Lett., 2007, 9,683.CrossRefPubMedGoogle Scholar
  21. 21.
    S. D. Kuduk, C. N. D. Marco, S. M. Pitzenberger, N. Tsou, Tetrahedron Lett., 2006, 47, 2377.CrossRefGoogle Scholar
  22. 22.
    C. Pierry, L. Zoute, P. Jubault, E. Pfund, T. Lequeux, D. Cahard, S. Couve-Bonnaire, X. Pannecoucke, Tetrahedron Lett., 2009, 50,264.CrossRefGoogle Scholar
  23. 23.
    V. L. Truong, J. Y. Pfeiffer, Tetrahedron Lett., 2009, 50, 1633.CrossRefGoogle Scholar
  24. 24.
    J. Liu, J. Hu, Future Med. Chem., 2009, 1,875.CrossRefPubMedGoogle Scholar
  25. 25.
    A. E. Sorochinsky, V. A. Soloshonok, J. Fluorine Chem., 2010, 131,127.CrossRefGoogle Scholar
  26. 26.
    M. T. Robak, M. A. Herbage, J. A. Ellman, Chem. Rev., 2010, 110, 3600.CrossRefGoogle Scholar
  27. 27.
    F. A. Davis, J. Org. Chem., 2006, 71, 8993.CrossRefPubMedGoogle Scholar
  28. 28.
    G. Liu, D. A. Cogan, J. A. Ellman, J. Am. Chem. Soc., 1997, 119, 9913.CrossRefGoogle Scholar
  29. 29.
    D. A. Cogan, G. Liu, K. Kim, B. J. Backes, J. A. Ellman, J. Am. Chem. Soc., 1998, 120, 8011.CrossRefGoogle Scholar
  30. 30.
    F. A. Davis, R. E. Reddy, J. M. Szewczyk, P. S. Portonovo, Tetrahedron Lett., 1993, 34, 6229.CrossRefGoogle Scholar
  31. 31.
    F. A. Davis, R. E. Reddy, J. M. Szewczyk, G. V. Reddy, P. S. Portonovo, H. Zhang, D. Fanelli, P. Zhou, P. J. Carroll, J. Org. Chem., 1997, 62, 2555.CrossRefPubMedGoogle Scholar
  32. 32.
    T.-K. Yang, R.-Y. Chen, D.-S. Lee, W.-S. Peng, Y.-Z. Jiang, A.-Q. Mi, T.-T. Jong, J. Org. Chem., 1994, 59,914.CrossRefGoogle Scholar
  33. 33.
    O. De Lucchi, V. Lucchini, C. Marchioro, G. Valle, G. Modena, J. Org. Chem., 1986, 51, 1457.CrossRefGoogle Scholar
  34. 34.
    R. Kawecki, Tetrahedron: Asymmetry, 2003, 14, 2827.CrossRefGoogle Scholar
  35. 35.
    E. S. Izmest´ev, D. V. Sudarikov, S. A. Rubtsova, P. A. Slepukhin, A. V. Kuchin, Russ. J. Org. Chem., 2012, 48,184.CrossRefGoogle Scholar
  36. 36.
    E. S. Izmest´ev, D. V. Sudarikov, S. A. Rubtsova, P. A. Slepukhin, A. V. Kuchin, Russ. J. Org. Chem., 2012, 48, 1407.CrossRefGoogle Scholar
  37. 37.
    E. S. Izmest´ev, D. V. Sudarikov, S. A. Rubtsova, P. A. Slepukhin, A. V. Kutchin, Russ. Chem. Bull., 2013, 62, 2367.CrossRefGoogle Scholar
  38. 38.
    D. V. Sudarikov, Yu. V. Krymskaya, P. A. Slepukhin, S. A. Rubtsova, A. V. Kutchin, Russ. Chem. Bull., 2016, 65, 1566.CrossRefGoogle Scholar
  39. 39.
    G. S. Prakash, M. Mandal, G. A. Olah, Angew. Chem., Int. Ed., 2001, 40,589.CrossRefGoogle Scholar
  40. 40.
    G. S. Prakash, M. Mandal, J. Am. Chem. Soc., 2002, 124, 6538.CrossRefPubMedGoogle Scholar
  41. 41.
    V. A. Soloshonok, H. Ohkura, A. Sorochinsky, N. Voloshin, A. Markovsky, M. Belik, T. Yamazaki, Tetrahedron Lett., 2002, 43, 5445.CrossRefGoogle Scholar
  42. 42.
    D. D. Staas, K. L. Savage, C. F. Homnick, N. N. Tsou, R. G. Ball, J. Org. Chem., 2002, 67, 8276.CrossRefPubMedGoogle Scholar
  43. 43.
    A. Banach, J. Scianowski, P. Ozimek, Phosphorus, Sulfur Silicon Relat. Elem., 2014, 189,274.CrossRefGoogle Scholar
  44. 44.
    O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard, H. Puschmann, J. Appl. Crystallogr., 2009, 42,339.CrossRefGoogle Scholar
  45. 45.
    G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., 2008, 64,112.CrossRefGoogle Scholar
  46. 46.
    H. D. Flack, Acta Crystallogr., Sect. A: Found. Crystallogr., 1983, 39, 876.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • D. V. Sudarikov
    • 1
  • Yu. V. Krymskaya
    • 1
  • N. O. Il’chenko
    • 1
  • P. A. Slepukhin
    • 2
    • 3
  • S. A. Rubtsova
    • 1
  • A. V. Kutchin
    • 1
  1. 1.Institute of Chemistry, Komi Scientific CenterUral Branch of the Russian Academy of SciencesSyktyvkar, Russian FederationRussia
  2. 2.Ya. Postovsky Institute of Organic SynthesisUral Branch of the Russian Academy of SciencesYekaterinburg, Russian FederationRussia
  3. 3.Ural Federal University named after the First President of Russia B. N. YeltsinYekaterinburg, Russian FederationRussia

Personalised recommendations