Advertisement

Russian Journal of General Chemistry

, Volume 88, Issue 4, pp 780–788 | Cite as

An Efficient Microwave-Assisted Synthesis of Novel 2-{4-[(3-Aryl-1,8-naphthyridin-2-yl)amino]phenyl}-1H-benzo[de]isoquinoline-1,3(2H)-diones and Their Antimicrobial Activity

  • B. Sakram
  • D. Ravi
  • K. Ashok
  • S. Rambabu
  • B. Sonyanaik
  • A. Kurumanna
Article
  • 11 Downloads

Abstract

The Buchwald–Hartwig amination reaction between 2-chloro-3-aryl-1,8-naphthyridines and 2-(4-aminophenyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione in the presence of the catalytic system Pd(PPh3)4 and the base KO-t-Bu in toluene was studied. The reaction was initiated by microwave irradiation. Highly efficient synthesis has been developed for 2-{4-[(3-aryl-1,8-naphthyridin-2-yl)amino]phenyl}-1H-benzo[de]isoquinoline-1,3(2H)-diones. Structures of the synthesized compounds were evaluated by IR, 1H and 13C NMR spectroscopy. All products were tested for antimicrobial activity against Escheria coli, Bacillus subtilis, Klebsiella pneumoniae, and Staphylococcus aureus.

Keywords

Antimicrobial activity C–N bond formation microwave irradiation molecular docking 1,8-naphthyridine Pd(PPh3)4 catalyst 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Notes

Acknowledgments

The authors are thankful to the Directors, CFRDOU, IICT, Hyderabad for providing IR, 1H, and 13C NMR, and mass spectral and analytical data. One of the author (B. Sakram) expresses thanks to the University Grant Commission, New-Delhi, India, for the financial support.

References

  1. 1.
    Gorecki, D.K.J. and Hawes, E.M., J. Med. Chem., 1977, vol. 20, p. 124. doi 10.1021/jm00211a026CrossRefGoogle Scholar
  2. 2.
    Bolhofer, W.A., Hoffman, J.M., Habecker, C.N., Pietruszkiewicz, A.M., Cragoe, E.J.Jr., and Torchiana, M.L., J. Med. Chem., 1979, vol. 22, p. 301. doi 10.1021/jm00189a016CrossRefGoogle Scholar
  3. 3.
    Roma, G., Di Braccio, M., Grossi, G., Mattioli, F., and Ghia, M., Eur. J. Med.Chem., 2000, vol. 35, p. 1021. doi 10.1016/S0223-5234(00)01175-2CrossRefGoogle Scholar
  4. 4.
    Gilis, P.M., Haemers, A., and Bollaert, W., J. Heterocycl. Chem., 1980, vol. 17, p. 717. doi 10.1002/jhet.5570170418CrossRefGoogle Scholar
  5. 5.
    Abbas, J.A. and Stuark, R.K., Expert. Opin. Investig. Drugs., 2012, vol. 21(8), p. 1223. doi 10.1517/13543784.2012.699038CrossRefGoogle Scholar
  6. 6.
    Marchese, A., Debbia, E.A., and Schito, G.C., J. Antimicrob. Chemother., 2000, vol. 46, p. 3. doi 10.1093/oxfordjournals.jac.a020891CrossRefGoogle Scholar
  7. 7.
    Fenlon, E.E., Murray, T.J., Baloga, M.H., and Zimmerman, S.C., J. Org. Chem., 1993, vol. 58, p. 6625. doi 10.1021/jo00076a021CrossRefGoogle Scholar
  8. 8.
    Piao, M.-Z. and Imafuku, K., J. Heterocycl. Chem., 1996, vol. 33, p. 389. doi 10.1002/jhet.5570330230CrossRefGoogle Scholar
  9. 9.
    Tsuzuki, Y., Tomita, K., Sato, Y., Kashimoto, S., and Chiba, K., Bioorg. Med. Chem. Lett., 2004, vol. 14, p. 3189. doi 10.1016/j.bmcl.2004.04.011CrossRefGoogle Scholar
  10. 10.
    Dianzani, C., Collino, M., Gallicchio, M., Di Braccio, M., Roma, G., and Fantozzi, R., J. Inflamm., 2006, vol. 3, p. 4. doi 10.1186/1476-9255-3-4CrossRefGoogle Scholar
  11. 11.
    Roma, G., Di Braccio, M., Grossi, G., Piras, D., Ballabeni, V., Tognolini, M., Bertoni, S., and Barocelli, E., Eur. J. Med. Chem., 2010, vol. 45, p. 352. doi 10.1016/j.ejmech.2009.10.020CrossRefGoogle Scholar
  12. 12.
    Leonard, J.T., Gangadhar, R., Gnanasam, S.K., Ramachandran, S., Saravanan, M., and Sridhar, S.K., Biol. Pharm. Bull., 2002, vol. 25, p. 798. PMID: 12081151.CrossRefGoogle Scholar
  13. 13.
    Ferrarini, P.L., Mori, C., Calderone, V., Calzolari, L., Nieri, P., Martinotti, E., and Saccomanni, G., Eur. J. Med. Chem., 1999, vol. 34, p. 505. doi 10.1016/S0223-5234(99)80099-3CrossRefGoogle Scholar
  14. 14.
    Ferrarini, P.L., Mori, C., Badawneh, M., Calderone, V., Calzolari, L., Loffredo, T., Martinotti, E., and Saccomanni, G., Eur. J. Med. Chem., 1998, vol. 33, p. 383. doi 10.1016/S0223-5234(98)80014-7CrossRefGoogle Scholar
  15. 15.
    Cotrel, C., Guyon, C., Roussel, G., and Taurand, G., US Patent 4753933, 1988.Google Scholar
  16. 16.
    Litvinov, V.P., Roman, S.V., and Dyachenko, V.D., Russ. Chem. Rev., 2000, vol. 69, p. 201. doi 10.1070/RC2000v069n03ABEH000553CrossRefGoogle Scholar
  17. 17.
    Louie, J. and Hartwig, J.F., Tetrahedron Lett., 1995, vol. 36, p. 3609. doi 10.1016/0040-4039(95)00605-CCrossRefGoogle Scholar
  18. 18.
    Christmann, U. and Vilar, R., Angew. Chem. Int. Ed., 2005, vol. 44, p. 366. doi 10.1002/anie.200461189CrossRefGoogle Scholar
  19. 19.
    O’Brien, C.J., Kantchev, E.A.B., Valente, C., Hadei, N., Chass, G.A., Lough, A., Hopkinson, A.C., and Organ, M.G., Chem.-Eur. J., 2006, vol. 12, p. 4743. doi 10.1002/chem.200690054CrossRefGoogle Scholar
  20. 20.
    Caddick, S., Tetrahedron, 1995, vol. 51, p. 10403. doi 10.1016/0040-4020(95)00662-RCrossRefGoogle Scholar
  21. 21.
    Galema, S.A., Chem. Soc. Rev., 1997, vol. 26, p. 233. doi 10.1039/CS9972600233CrossRefGoogle Scholar
  22. 22.
    Bose, A.K., Banik, B.K., Lavlinskaia, N., Jayaraman, M., and Manhas, M.S., Chemtech., 1997, vol. 27, p. 18.Google Scholar
  23. 23.
    (a) Sakram, B., Rambabu, S., Ashok, K., Sonyanaik, B., and Ravi, D., Russ. J. Gen. Chem, 2016, vol. 87, no. 12, p. 2737. doi 10.1134/S1070363216120343.CrossRefGoogle Scholar
  24. (b).
    Sakram, B., Ashok, K., Rambabu, S., Sonyanaik, B., and Ravi, D., Russ. J. Gen. Chem, 2017, vol. 87, no. 8, p. 1794. doi 10.1134/S1070363217080266.CrossRefGoogle Scholar
  25. (c).
    Sakram, B., Sonyanaik, B., Ashok, K., Rambabu, S., Ravi, D., Kurumanna, A., and Shyam, P., Res. Chem. Intermed., 2017, vol. 43, p. 1881.CrossRefGoogle Scholar
  26. 24.
    Mogilaiah, K., Ramesh Babu H., and Vasudeva Reddy, N., Synth. Commun., 2002, vol. 32, p. 2377. doi 10.1081/SCC-120006009CrossRefGoogle Scholar
  27. 25.
    Choi C.S., Jeon K.S., Jeong W.C., and Lee K.H., Bull. Korean Chem. Soc., 2010, vol. 31, no. 5, p. 1375. doi 10.5012/bkcs.2010.31.5.1375CrossRefGoogle Scholar
  28. 26.
    Morris, G.M., Huey, R., Lindstrom, W., Sanner, M.F., Belew, R.K., Goodsell, D.S, and Olson, A.J., J Comput. Chem., 2009, vol. 30, no. 16, p. 2785. doi 10.1002/jcc.21256CrossRefGoogle Scholar
  29. 27.
    Goodsell, D.S. and Olson, A.J., Proteins, 1990, vol. 8, p. 195. doi 10.1002/prot.34008030CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  • B. Sakram
    • 1
  • D. Ravi
    • 1
  • K. Ashok
    • 1
  • S. Rambabu
    • 1
  • B. Sonyanaik
    • 1
  • A. Kurumanna
    • 1
  1. 1.Department of ChemistryOsmania UniversityHyderabadIndia

Personalised recommendations