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Pharmaceutical Chemistry Journal

, Volume 52, Issue 12, pp 969–974 | Cite as

Synthesis and Antimicrobial Activity of 3-Phenyl-1-Methylquinolin-2-One Derivatives

  • O. V. Elenich
  • R. Z. Lytvyn
  • O. V. Blinder
  • O. V. Skripskaya
  • O. S. Lyavinets
  • Kh. E. Pitkovych
  • M. D. ObushakEmail author
  • P. I. Yagodinets
Article
  • 65 Downloads

A series of quaternary salts were obtained by reacting 3-(4-bromoacetylphenyl)-1-methylquinolin-2(1H)-one with Py, 4-methylpyridine, quinoline, benzo[f]quinoline, and triphenylphosphine. Derivatives of thiazole, imidazo[1,2-a]pyridine, and imidazo[1,2-a]pyrimidine were produced using dinucleophilic reagents. Several of the synthesized compounds possessed high antimicrobial activity, indicating that further research on this series of compounds was promising.

Keywords

quinolin-2-one derivatives synthesis antimicrobial activity quaternary salts bromoketones heterocyclization 

References

  1. 1.
    M. F. Grundon, The Alkaloids: Quinoline Alkaloids Related to Anthranilic Acid, Vol. 32, Academic, London (1968), pp. 341 – 439.Google Scholar
  2. 2.
    N. Nishiwaki, M. Sakashita, M. Azuma, et al., Tetrahedron, 58, 473 – 478 (2002).CrossRefGoogle Scholar
  3. 3.
    C.-S. Jia, Y.-W. Dong, S.-J. Tu, et al., Tetrahedron, 63, 892 – 897 (2007).CrossRefGoogle Scholar
  4. 4.
    A. Kumar, J. Fernandes, and P. Kumar, J. Pharm. Pharm. Sci., 3(2), 1267 – 1277 (2014).Google Scholar
  5. 5.
    R. I. H. Al-Bayati and M. F. Radi, Afr. J. Pure Appl. Chem., 4(10), 228 – 232 (2010).Google Scholar
  6. 6.
    I. G. Tikhonova, I. I. Baskin, V. A. Palyulin, et al., J. Med. Chem., 46(9), 1609 – 1616 (2003).CrossRefGoogle Scholar
  7. 7.
    G. Leclerc, G. Marciniak, N. Decker, et al., J. Med. Chem., 29(12), 2427 – 2432 (1986).CrossRefGoogle Scholar
  8. 8.
    J. Milecki, S. P. Baker, K. M. Standifer, et al., J. Med. Chem., 30(9), 1563 – 1566 (1987).CrossRefGoogle Scholar
  9. 9.
    B. S. Jayashree, S. Thomas, and Y. Nayak, Med. Chem. Res., 19, 193 – 209 (2010).CrossRefGoogle Scholar
  10. 10.
    F. Melani, L. Cecchi, G. Palazzino, et al., J. Med. Chem., 29(2), 291 – 295 (1986).CrossRefGoogle Scholar
  11. 11.
    D. A. Sabbah, W. Wang, Y. Dong, et al., Bioorg. Med. Chem., 20, 7175 – 7183 (2012).CrossRefGoogle Scholar
  12. 12.
    C. Ito, M. Itoigawa, A. Furukawa, et al., J. Nat. Prod., 67(11), 1800 – 1803 (2004).CrossRefGoogle Scholar
  13. 13.
    H. S. Chung and W. S. Woo, J. Nat. Prod., 64(12), 1579 – 1580 (2001).CrossRefGoogle Scholar
  14. 14.
    T. O. Tsapko, I. S. Gritsenko, V. O. Zubkov, et al., Visn. Farm., 3(59), 7 – 10 (2009); T. O. Tsapko, I. S. Grytsenko, V. O. Zubkov, et al., News Pharm., 3(59), 7 – 10 (2009).Google Scholar
  15. 15.
    JP Pat. 2,003,840; Chem. Abstr., 73, 64584u (1970).Google Scholar
  16. 16.
    H. Nishimura, Y. Nagai, and K. Nakamura, JP Pat. 44016373, Jul. 19, 1969; Chem. Abstr., 71, 124273b (1969).Google Scholar
  17. 17.
    B. Joseph, F. Darro, et al., FR Pat. 2,781,218, Jan. 21, 2000; Ref. Zh. Khim., 16 – 190.80P (2000).Google Scholar
  18. 18.
    S. Tamada, T. Fujioka, et al., US Pat. 4,886,809, Dec. 12, 1989; Ref. Zh. Khim., 18065P (1991).Google Scholar
  19. 19.
    JP Pat. 2117662, 1990; Ref. Zh. Khim., 20046P (1991).Google Scholar
  20. 20.
    A. Doleans-Jordheim, J. B. Veron, O. Fendrich, et al., ChemMedChem, 8, 1 – 7 (2013).CrossRefGoogle Scholar
  21. 21.
    J. Roy and A. P. Bhaduri, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 16(8), 744 – 745 (1978).Google Scholar
  22. 22.
    M. A. Alonso, M. Blanco, C. Avendano, et al., Heterocycles, 36, 2315 – 2325 (1993).CrossRefGoogle Scholar
  23. 23.
    B. Joseph, F. Darro, A. Behard, et al., J. Med. Chem., 45, 2543 – 2555 (2002).CrossRefGoogle Scholar
  24. 24.
    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).Google Scholar
  25. 25.
    Handbook for Experimental (Preclinical) Studies of New Drugs [in Russian], Biont, Moscow (2000), pp. 264 – 273.Google Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • O. V. Elenich
    • 1
  • R. Z. Lytvyn
    • 2
  • O. V. Blinder
    • 3
  • O. V. Skripskaya
    • 1
  • O. S. Lyavinets
    • 1
  • Kh. E. Pitkovych
    • 2
  • M. D. Obushak
    • 2
    Email author
  • P. I. Yagodinets
    • 1
  1. 1.Yuriy Fedkovych Chernivtsi National UniversityChernivtsiUkraine
  2. 2.Ivan Franko National University of LvivLvivUkraine
  3. 3.L. I. Medved Research Center of Preventive Toxicology, Food and Chemical Safety, Department of Medical and Environmental Problems, Ministry of HealthChernivtsiUkraine

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