Skip to main content
SpringerLink
Log in

Synthesis and Antimicrobial Activity of 4-(4-Acetylphenyl)-3-Hydroxy-2H-Chromen-2-One Derivatives

  • Published:
Pharmaceutical Chemistry Journal Aims and scope

Reactions of 4-(4-bromoacetylphenyl)-3-hydroxy-2H-chromen-2-one with Py, 4-methylpyridine, quinoline, and benzo[f]quinoline produced quaternary salts; with dinucleophiles, derivatives of thiazole, imidazo[1,2-a]pyridine, and imidazo[1,2-a]pyrimidine. Several of the target compounds exhibited high antimicrobial activity that indicated further research on these compounds is warranted.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. L. Verotta, E. Lovaglio, G. Vidari, et al., Phytochemistry, 65, 2867 – 2879 (2004).

    Article  CAS  Google Scholar 

  2. C. Billard, F. Menasria, C. Quiney, et al., Exp. Hematol., 36, 1625 – 1633 (2008).

    Article  CAS  Google Scholar 

  3. C. Rappl, P. Barbier, V. Bourgarel-Rey, et al., Biochemistry, 45(30), 9210 – 9218 (2006).

    Article  CAS  Google Scholar 

  4. R. Argotte-Ramos, G. Ramirez-Avila, M. C. Rodriguez-Gutierrez, et al., J. Nat. Prod., 69, 1442 – 1444 (2006); doi https://doi.org/10.1021/np060233p.

    Article  CAS  PubMed  Google Scholar 

  5. A. M. Zhyvoloup, S. M. Yarmoluk, M. M. Garazd, et al., Biopolym. Cell, 14(6), 553 – 558 (1998); http: //www.biopolymers.org.ua/pdf/uk/14/6/553/biopolym.cell-1998-14-6-553-uk.pdf.

    Article  Google Scholar 

  6. J. Crecente-Campo, M. P. Vazquez-Tato, and J. A. Seijas, Eur. J. Org. Chem., 21, 4130 – 4135 (2010).

    Article  Google Scholar 

  7. S. Combes, P. Barbier, S. Douillard, et al., J. Med. Chem., 54, 3153 – 3162 (2011).

    Article  CAS  Google Scholar 

  8. J.-T. Pierson, A. Dumetre, S. Hutter, et al., Eur. J. Med. Chem., 45, 864 – 869 (2010).

    Article  CAS  Google Scholar 

  9. C. Bailly, C. Bal, P. Barbier, et al., J. Med. Chem., 46(25), 5437 – 5444 (2003).

    Article  CAS  Google Scholar 

  10. T. Kawate, N. Iwase, M. Shimizu, et al., Bioorg. Med. Chem. Lett., 23(22), 6052 – 6059 (2013).

    Article  CAS  Google Scholar 

  11. G. Feuer, Prog. Med. Chem., 10, 85 – 158 (1974).

    Article  CAS  Google Scholar 

  12. M. Khoobi, M. Alipour, S. Zarei, et al., Chem. Commun., 48, 2985 – 2987 (2012).

    Article  CAS  Google Scholar 

  13. I.-T. Hwang, S.-A. Lee, J.-S. Hwang, and K.-I. Lee, Molecules, 16, 6313 – 6321 (2011).

    Article  CAS  Google Scholar 

  14. M. M. Garazd, Ya. L. Garazd, and V. P. Khilya, Chem. Nat. Compd., 41(3), 245 – 271 (2005).

    Article  CAS  Google Scholar 

  15. Z. Karimi-Jaberi and L. Zarei, Acta Chim. Slov., 60, 178 – 183 (2013).

    CAS  PubMed  Google Scholar 

  16. H. R. Shaterian and M. Aghakhanizadeh, Chin. J. Catal., 34, 1690 – 1696 (2013).

    Article  CAS  Google Scholar 

  17. B. Karami, S. Khodabakhshi, and K. Eskandari, Tetrahedron Lett., 53, 1445 – 1446 (2012).

    Article  CAS  Google Scholar 

  18. B. C. Raju, T. H. Babu, and J. M. Rao, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 48, 120 – 123 (2009).

    Google Scholar 

  19. D. M. X. Donnelly, J.-P. Finet, P. J. Guiry, et al., Synth. Commun., 29(15), 2719 – 2730 (1999).

    Article  CAS  Google Scholar 

  20. G. M. Boland, D. M. X. Donnelly, J.-P. Finet, et al., J. Chem. Soc., Perkin Trans. 1, 2591 – 2597 (1996).

  21. L. Schio, F. Chatreaux, and M. Klich, Tetrahedron Lett., 41, 1543 – 1547 (2000).

    Article  CAS  Google Scholar 

  22. A. Yu. Fedorov, A. V. Nyuchev, and I. P. Beletskaya, Khim. Geterotsikl. Soedin., 48(1), 175 – 186 (2012); A. Yu. Fedorov, A. V. Nyuchev, and I. P. Beletskaya, Chem. Heterocycl. Compd., 48(1), 166 – 178 (2012).

  23. O. V. Skripskaya, N. O. Feilo, A. O. Neshchadin, et al., Zh. Org. Khim., 49(11), 1673 – 1678 (2013); O. V. Skripskaya, N. O. Feilo, A. O. Neshchadin, et al., Russ. J. Org. Chem., 49(11), 1655 – 1660 (2013).

  24. O. V. Elenich, R. Z. Lytvyn, O. V. Blinder, et al., Khim.-farm. Zh., 52(12), 7 – 11 (2018); O. V. Elenich, R. Z. Lytvyn, O. V. Blinder, et al., Pharm. Chem. J., 52(12), 969 – 974 (2018).

  25. D. P. Becker, D. L. Flynn, et al., US Pat. 5,260,303, Nov. 1, 1993; Chem. Abstr., 118, 254908n (1993).

  26. J. J. Kaminski, C. Puchalski, D. M. Solomon, et al., J. Med. Chem., 32, 1686 – 1700 (1989).

    Article  CAS  Google Scholar 

  27. K. Srimanth, V. R. Rao, and D. R. Krishna, Arzneim. Forsch., 52, 388 – 392 (2002).

    CAS  Google Scholar 

  28. I. V. Orlenko, S. N. Kovalenko, I. A. Zhuravel’, et al., Fiziol. Akt. Rechovini, 32(2), 25 – 28 (2001); I. V. Orlenko, S. M. Kovalenko, I. O. Zhuravel, et al., Physiol. Act. Subst., 32(2), 25 – 28 (2001).

  29. Guide for Experimental (Preclinical) Studies of New Drugs [in Russian], Biont, Moscow, 2000, pp. 264 – 273.

Download references

Author information

Authors and Affiliations

  1. Yu. Fedkovych Chernivtsi National University, Chernivtsi, 58012, Ukraine

    O. V. Rusnak, O. V. Skripskaya & P. I. Yagodinets

  2. Ivan Franko National University of Lviv, Lviv, 79005, Ukraine

    R. Z. Lytvyn, Kh. E. Pitkovych & M. D. Obushak

  3. Bukovinian State Medical University, Chernivtsi, 58000, Ukraine

    O. O. Blinder

Authors
  1. O. V. Rusnak
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. R. Z. Lytvyn
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. O. V. Skripskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. O. O. Blinder
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Kh. E. Pitkovych
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. P. I. Yagodinets
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. M. D. Obushak
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to M. D. Obushak.

Additional information

Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 53, No. 9, pp. 20 – 25, September, 2019.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Rusnak, O.V., Lytvyn, R.Z., Skripskaya, O.V. et al. Synthesis and Antimicrobial Activity of 4-(4-Acetylphenyl)-3-Hydroxy-2H-Chromen-2-One Derivatives. Pharm Chem J 53, 797–802 (2019). https://doi.org/10.1007/s11094-019-02082-0

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11094-019-02082-0

Keywords

Search

Navigation