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Vol. 30 No. 11 (2018): Vol 30 Issue 11

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A Mild and Efficient Copper-Mediated N-Arylation of 6-Azauracil with Corresponding Boronic Acids and their Antibacterial Activity

https://doi.org/10.14233/ajchem.2018.21491
Kali Charan Gulipalli
Department of Chemistry, Koneru Lakshmaiah Education Foundation, Green fields, Vaddeswaram, Guntur-522 502, India
Srinu Bodige
Department of Chemistry, Koneru Lakshmaiah Education Foundation, Green fields, Vaddeswaram, Guntur-522 502, India
Parameshwar Ravula
Department of Pharmaceutical Chemistry, Gurunanak Institutions Technical Campus, School of Pharmacy, Ibrahimpatnam-501 506, India
R. Sekhar Bolla
Department of Chemistry, Koneru Lakshmaiah Education Foundation, Green fields, Vaddeswaram, Guntur-522 502, India
Srinivas Endoori
Department of Chemistry, Koneru Lakshmaiah Education Foundation, Green fields, Vaddeswaram, Guntur-522 502, India
Purna Koteswara Rao Cherukumalli
Department of Chemistry, Koneru Lakshmaiah Education Foundation, Green fields, Vaddeswaram, Guntur-522 502, India
Nareshvarma Seelam
Department of Chemistry, Koneru Lakshmaiah Education Foundation, Green fields, Vaddeswaram, Guntur-522 502, India

Corresponding Author(s) : Nareshvarma Seelam

nareshvarma.klu@gmail.com

Asian Journal of Chemistry, Vol. 30 No. 11 (2018): Vol 30 Issue 11

Abstract

A convenient synthetic strategy is reported for the synthesis of N-arylated 6-azauracil through Chan-Lam cross-coupling. A variety of N-arylated 6-azauracil derivatives were synthesized in moderate to good yields by cross-coupling of 6-azauracil with arylboronic acids in the presence of Cu(OAc)2 and pyridine. However the arylation position is confirmed in the case of 2-(3,5-dichlorophenyl)-1,2,4-triazine- 3,5(2H,4H)-dione (3a), by preparing the compound in a traditional method and compared the chemical shift of the NH proton at N-3 position. Further, the synthesized compounds were screened for their antibacterial activity using agar well diffusion method. The results revealed that most of the synthesized moieties possessing promising therapeutic nature.

Keywords

6-Azauracil N-arylation Chan-Lam cross-coupling Copper acetate Antibacterial activity
Gulipalli, K. C., Bodige, S., Ravula, P., Bolla, R. S., Endoori, S., Rao Cherukumalli, P. K., & Seelam, N. (2018). A Mild and Efficient Copper-Mediated N-Arylation of 6-Azauracil with Corresponding Boronic Acids and their Antibacterial Activity. Asian Journal of Chemistry, 30(11), 2495–2501. https://doi.org/10.14233/ajchem.2018.21491
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References
  1. R.E. Handschumacher, P. Calabresi, A.D. Welch, V. Bono, H. Fallon and E. Frei, Cancer Chemother. Rep., 21, 1 (1962).
  2. T.R. Walters, R.J.A. Aur, K. Hernandez, T. Vietti and D. Pinkel, Cancer, 29, 1057 (1972); https://doi.org/10.1002/1097-0142(197204)29:4<1057::AIDCNCR2820290455>3.0.CO;2-Q.
  3. B. Rada and D. Blaskovic, Acta Virol., 10, 1 (1966).
  4. D. Falke and B. Rada, Acta Virol., 14, 115 (1970).
  5. I. Alexeeva, L. Palchikovskaya, A. Shalamay, L. Nosach, V. Zhovnovataya, O. Povnitsa and N. Dyachenko, Acta Biochim. Polon., 47, 95 (2000).
  6. Y. Kabbaj, H.B. Lazrek, J.L. Barascut and J.L. Imbach, Nucleos. Nucl. Nucl. Acids, 24, 161 (2005); https://doi.org/10.1081/NCN-55695.
  7. P. Calabresi and R.W. Turner, Ann. Intern. Med., 64, 352 (1966); https://doi.org/10.7326/0003-4819-64-2-352.
  8. R. Gunther, Wien. Med. Wochenschr., 117, 985 (1967).
  9. R.C. Deconti and P. Calabresi, Ann. Intern. Med., 73, 575 (1970); https://doi.org/10.7326/0003-4819-73-4-575.
  10. B.L. Mylari, M.W. Miller, H.L. Howes, S. Figdor, J.E. Lynch and R.C. Koch, J. Med. Chem., 20, 475 (1977); https://doi.org/10.1021/jm00214a003.
  11. M.W. Miller, B.L. Mylari, H.L. Howes, J.E. Lynch, M.J. Lynch and R.C. Koch, J. Med. Chem., 22, 1483 (1979); https://doi.org/10.1021/jm00198a010.
  12. J.W. St Geme and H.L. Martin, Infect. Immun., 11, 915 (1975).
  13. K.A. Steffenhagen, B.C. Easterday and G.J. Galasso, J. Infect. Dis., 133, 603 (1976); https://doi.org/10.1093/infdis/133.6.603.
  14. J.J. Li, L.H. Mitchell and R.L. Dow, Bioorg. Med. Chem. Lett., 20, 306 (2010); https://doi.org/10.1016/j.bmcl.2009.10.109.
  15. O. Vanparijs, L. Hermans, L. Van der Flaes, K. Vlaminck and R. Marsboom, Tijdschr. Diergeneeskd., 113, 190 (1988).
  16. J. Slouka, Monatsh. Chem., 96, 134 (1965); https://doi.org/10.1007/BF00912302.
  17. E. Riguet, B. Campo, A. Gibelin and K. Mhalla, Novel Triazinedione Derivatives as GABA-β receptor Modulators, WO2008056257 A2 (2008).
  18. I. Leroy, E. Dupont-Passelaigue, K. Valeille, Y. Rival and D. Junquero, Derivatives of Triazines and Uracils, Their Preparation and Their Application in Human Therapeutics, WO2010006962 A1 (2010).
  19. Z. Rankovic, J. Cai, X. Fradera, M. Dempster, A. Mistry, A. Mitchell, C. Long, E. Hamilton, A. King, S. Boucharens, C. Jamieson, J. Gillespie, I. Cumming, J. Uitdehaag and M.V. Zeeland, Bioorg. Med. Chem. Lett., 20, 1488 (2010); https://doi.org/10.1016/j.bmcl.2010.01.116.
  20. P.Y.S. Lam, C.G. Clark, S. Saubern, J. Adams, M.P. Winters, D.M.T. Chan and A. Combs, Tetrahedron Lett., 39, 2941 (1998); https://doi.org/10.1016/S0040-4039(98)00504-8.
  21. D.M.T. Chan, K.L. Monaco, R.P. Wang and M.P. Winters, Tetrahedron Lett., 39, 2933 (1998); https://doi.org/10.1016/S0040-4039(98)00503-6.
  22. J.W. Mcfarland, C.B. Cooper and D.M. Newcomb, J. Med. Chem., 34, 1908 (1991); https://doi.org/10.1021/jm00110a023.
  23. M.W. Miller, 2-Phenyl-as-triazine-3,5(2H,4H)diones, US Patent 3912723 A (1975).
  24. M.W. Miller, B.L. Mylari, H.L. Howes, S.K. Figdor, M.J. Lynch, J.E. Lynch and R.C. Koch, J. Med. Chem., 23, 1083 (1980); https://doi.org/10.1021/jm00184a005.
  25. E. Shivarani, R. Parameswar, V. Harinadhababu and Y.S. Ranganath, Int. J. Pharm. Sci., 4, 424 (2012).
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