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New N-Mannich bases obtained from isatin and piperazine derivatives: the synthesis and evaluation of antimicrobial activity

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Chemistry of Heterocyclic Compounds Aims and scope

A Mannich reaction of isatin with monosubstituted piperazines in the presence of aqueous formaldehyde was used to synthesize new, as well as two previously described derivatives of 1-piperazinomethylisatins, which were further converted to isoindigo derivatives. The antimicrobial activity of the obtained heterocycles was evaluated.

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References

  1. Shvekhgeimer, M. G.-A. Chem. Heterocycl. Compd. 1996, 32, 249. [Khim. Geterotsikl. Soedin. 1996, 291.]

  2. Shvekhgeimer, M. G.-A. Chem. Heterocycl. Compd. 2004, 40, 257. [Khim. Geterotsikl. Soedin. 2004, 323.]

  3. Musin, L. I.; Bogdanov, A. V.; Mironov, V. F. Chem. Heterocycl. Compd. 2015, 51, 421. [Khim. Geterotsikl. Soedin. 2015, 51, 421.]

  4. Bogdanov, A. V.; Musin, L. I.; Mironov, V. F. ARKIVOC 2015, (vi), 362.

  5. Lashgari, N.; Ziarani, Gh. M. ARKIVOC 2012, (i), 277.

  6. Prakash, C. R.; Raja, S. Mini-Rev. Med. Chem. 2012, 12, 98.

    Article  CAS  Google Scholar 

  7. Vine, K. L.; Matesic, L.; Locke, J. M.; Skropeta, D. In Advances in Anticancer Agents in Medicinal Chemistry, Prudhomme, M., Ed.; Bentham Science Publishers: Sharjah, 2013, p. 254.

    Chapter  Google Scholar 

  8. Pandeya, S. N.; Sriram, D.; Yogeeswari, P.; Ananthan, S. Chemotherapy 2001, 47, 266.

    Article  CAS  Google Scholar 

  9. Pandeya, S. N.; Smitha, S.; Stables, J. P. Arch. Pharm. Med. Chem. 2002, 4, 129.

    Article  Google Scholar 

  10. Cheah, W. Ch.; Black, D. StC.; Goh, W. K.; Kumar, N. Tetrahedron Lett. 2008, 49, 2965.

    Article  CAS  Google Scholar 

  11. Cheah, W. Ch.; Wood, K.; Black, D. StC.; Kumar, N. Tetrahedron 2011, 67, 7603.

    Article  CAS  Google Scholar 

  12. Mahida, V. P.; Patel, M. P. Chin. Chem. Lett. 2014, 25, 601.

    Article  CAS  Google Scholar 

  13. Sriram, Dh.; Yogeeswari, P.; Basha, J. S; Radha, D. R.; Nagaraja, V. Bioorg. Med. Chem. 2005, 13, 5774.

    Article  CAS  Google Scholar 

  14. Raja, S.; Prakash, Ch. R. Arch. Pharm. Res. 2013, 36, 411.

    Article  CAS  Google Scholar 

  15. Feng, L.-Sh.; Liu, M.-L.; Zhang, Sh.; Chai, Y.; Wang, B.; Zhang, Y.-B.; Lv, K.; Guan, Y.; Guo, H.-Y.; Xiao, Ch.-L. Eur. J. Med. Chem. 2011, 46, 341.

    Article  CAS  Google Scholar 

  16. Taher, A. T.; Khalil, N. A.; Ahmed E. M. Arch. Pharm. Res. 2011, 34, 1615.

    Article  CAS  Google Scholar 

  17. Solomon, V. R.; Hua, Ch.; Lee, H. Bioorg. Med. Chem. 2010, 18, 1563.

    Article  CAS  Google Scholar 

  18. Chiyanzu, I.; Clarkson, C.; Smith, P. J.; Lehman, J.; Gut, J.; Rosenthal, Ph. J.; Chibale, K. Bioorg. Med. Chem. 2005, 13, 3249.

    Article  CAS  Google Scholar 

  19. Ravichandran, V.; Mohan, S.; Kumar K. S. ARKIVOC 2007, (xiv), 51.

  20. Varma, R. S.; Nobles, W. L. J. Pharm. Sci. 1975, 64, 881.

    Article  CAS  Google Scholar 

  21. Kupinic, M.; Medic-Saric, M.; Movrin, M.; Maysinger, D. J. Pharm. Sci. 1979, 68, 459.

    Article  CAS  Google Scholar 

  22. Musin, L. I.; Bogdanov, A. V.; Il'in, A. V.; Mironov, V. F. J. Heterocycl. Chem. 2014, 51, 1027.

    Article  Google Scholar 

  23. Tramontini, M. Synthesis 1973, 703.

  24. Reissert, A.; Handeler, A. Chem. Ber. 1924, 57, 989.

    Article  Google Scholar 

  25. National Committee for Clinical Laboratory Standards, Methods for dilution antimicrobial susceptibility. Tests for bacteria that grow aerobically – sixth edition: approved standard, M7-A5, NCCLS, Wayne, Pa., USA, 2000.

  26. National Committee for Clinical Laboratory Standards, Reference method for broth dilution antifungal susceptibility testing of conidium-forming filamentous fungi: proposed standard, M38-P, NCCLS, Wayne, Pa., USA, 1998.

  27. Sheldrick, G. M. Acta Crystallogr., Sect. A.: Found. Crystallogr. 2008, A64, 112.

    Article  Google Scholar 

  28. Sheldrick, G. M. SADABS; Bruker AXS, Inc.: Madison, 1997.

  29. Farrugia, L. J. J. Appl. Cryst. 1997, 30, 565.

    Article  CAS  Google Scholar 

  30. Spek, A. L. Acta Crystallogr., Sect. A.: Found. Crystallogr. 1990, A46, 34.

    Google Scholar 

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Authors and Affiliations

  1. A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, 8 Arbuzova St., Kazan, 420088, Russia

    Andrei V. Bogdanov, Al’bina M. Vazykhova, Nadezhda R. Khasiyatullina, Dmitry B. Krivolapov, Alexey B. Dobrynin, Alexandra D. Voloshina & Vladimir F. Mironov

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  1. Andrei V. Bogdanov
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  2. Al’bina M. Vazykhova
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  3. Nadezhda R. Khasiyatullina
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  4. Dmitry B. Krivolapov
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  5. Alexey B. Dobrynin
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  6. Alexandra D. Voloshina
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  7. Vladimir F. Mironov
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Corresponding author

Correspondence to Andrei V. Bogdanov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(1), 25–30

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Bogdanov, A.V., Vazykhova, A.M., Khasiyatullina, N.R. et al. New N-Mannich bases obtained from isatin and piperazine derivatives: the synthesis and evaluation of antimicrobial activity. Chem Heterocycl Comp 52, 25–30 (2016). https://doi.org/10.1007/s10593-016-1826-6

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  • DOI: https://doi.org/10.1007/s10593-016-1826-6

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