Skip to main content
SpringerLink
Log in

Kumada cross coupling reaction based synthesis, antimicrobial and computational studies of 6-aryl-2-phenyl-3-methylquinazolin-4(3H)-ones

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

Nickel catalyzed Kumada cross coupling reaction, a novel synthetic method for the synthesis of 6-aryl-2-phenyl-3-methylquinazolin-4(3H)-ones (6a–6i), was carried out by condensing 6-iodo-2-phenyl-3-methyl-quinazolin-4(3H)-one (4) with various 6-aryl/heteroaryl Grignard reagents. Molecular properties of compounds 4 and 6a–6i were studied using semiempirical PM3 computational method. The optimized geometry of the product 6 indicated that the aryl group at the position 6 was not coplanar with respect to either quinazolinone ring or phenyl group at 2 position. Compounds 6a–6i were screened for their activity against bacteria and fungi.

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. Negishi, E., Angew. Chem., Int. Ed., 2011, vol. 50, pp. 6738–6764.

    Article  CAS  Google Scholar 

  2. Nicolaou, K.C., Bulger, P.G., and Sarlah, D., Angew. Chem., Int. Ed., 2005, vol. 44, pp. 4442–4489.

    Article  CAS  Google Scholar 

  3. Corbet, J. and Mignani, G., Chem. Rev., 2006, vol. 106, pp. 2651–2710.

    Article  CAS  Google Scholar 

  4. Magano, J. and Dunetz, J.R., Chem. Rev., 2011, vol. 111, pp. 2177–2250.

    Article  CAS  Google Scholar 

  5. Johansson Seechurn, C.C.C., Kitching, M.O., Colacot, T.J., and Snieckus, V., Angew. Chem., Int. Ed., 2012, vol. 51, pp. 5062–5085.

    Article  CAS  Google Scholar 

  6. Jana, R., Pathak, T.P., and Sigman, M.S., Chem. Rev., 2011, vol. 111, pp. 1417–149.

    Article  CAS  Google Scholar 

  7. Kohei, T., Koji, S., and Makoto, K., J. Am. Chem. Soc., 1972, vol. 94, pp. 4374–4376.

    Article  Google Scholar 

  8. Corriu, R.J.P., and Masse, J.P., J. Chem. Soc., Chem. Commun., 1972, p. 144a.

    Google Scholar 

  9. Vechorkin, O., Proust, V., and Hu, X., J. Am. Chem. Soc., 2009, vol. 131, pp. 9756–9766.

    Article  CAS  Google Scholar 

  10. Neslihan, S., David, S. A., Eric, B., Dominique, M., Ozdemir, I., Cemal, K., and Loic T., Eur. J. Org. Chem., 2013, pp. 4443–4449.

    Google Scholar 

  11. Berding, J., Lutz, M., and Spek, A.L., Organometallics, 2009, vol. 28, pp. 1845–1854.

    Article  CAS  Google Scholar 

  12. Kiss A., Hell Z., and Bálint M., Org. Biomol. Chem., 2010, vol. 21, pp. 331–335.

    Article  Google Scholar 

  13. Selvam, P.T., Kumar, P.V., and Vijayaraj, P., Res. Pharma, 2011, vol. 1, no. 1, pp. 1–21.

    Google Scholar 

  14. Jackman, A.L., Kimball, R., Aherne, G.W., Brunton, L., Jansen, G., Stephens, T.C., Smith, M.N., Ardleworth, J.M., and Boyle, F.T., Clinical Cancer Res., 1997, pp. 911–921.

    Google Scholar 

  15. Napier, S.E., Letourneau, J.J., Ansari, N., Auld, D.S., Baker, J., Best, S., Campbell-Wan, L., Chan, R., Craighead, M., Desai, H., Ho, K.K., MacSweeney, C., Milne, R., Richard Morphy, J., Neagu, I., Ohlmeyer, M.H, Pick, J., Presland, J., Riviello, C., Zanetakos, H.A, Zhao, J., and Webb, M.L., Bioorg. Med. Chem. Lett., 2011, vol. 21, pp. 3813–3817.

    Article  CAS  Google Scholar 

  16. Garlapati, R., Pottabathini, N., Gurram, V., Kasani, K.S., Gundla, R., Thulluri, C., Machiraju, P.K., Chaudhary, A.B., Addepally, U., Dayam, R., Chunduri, V.R., and Patro, B., Org. Bimol. Chem., 2013, vol. 11, pp. 4778–91.

    Article  CAS  Google Scholar 

  17. Lawson, E.C., Kinney, W.A., Costanzo, M.J., Hoekstra, W.J., Kauffman, J.A., Luci, D.K., Santulli, R., Tounge, B.A., Yabut, S.C., and Gordon, P.A., Lett. Drug Design Discov., 2004, vol. 1, no. 1, pp. 14–18.

    Article  CAS  Google Scholar 

  18. Joachim, R., William, P.E., Stephen, O., Philip, D.G.C., Philip, L.W., Michael, B., Donald, E.B., Brian, T.B., Georgiy, B., Libing, C., Chih-Yuan, C., Thomas, H.C., Zahra, F., Wenlang, F., Uday, R.K., James, A.K., Xiao-Gao, L., Derek, B.L., Andrea, C.M., Martin, M., Astrid, A.O., Philip, D.R., Robert, W.S., Tatiana, E.S., Alexandros, V., Weifeng, T., Lei, W., Lin, Y., Stephen, J.G., James, N.L., Laurel, J.S., and William, H.B., J. Med. Chem., 2007, vol. 50, pp. 5202–5216.

    Article  Google Scholar 

  19. Napier, S.E., Letourneau, J.J., Ansari, N., Auld, D.S., Baker, J., Best, S., Campbell-Wan, L., Chan, R., Craighead, M., Desai, H., Koc-Kan, H., MacSweeney, C., Milne, R., Morphy, J.R., Neagu, I., Ohlmeyer, M.H.J., Pick, J., Presland, J., Riviello, C., Zanetakos, H.A., Zhao, J.O., and Webbb, M.L., Bioorg. Med. Chem. Lett., 2011, vol. 21, pp. 3813–3817.

    Article  CAS  Google Scholar 

  20. Fang, X., Chen, Y.T., Sessions, E.H., Chowdhury, S., Vojkovsky, T., Yin, Y., Pocas, J.R., Grant, W., Schroter, T., Lin, L., Ruiz, C., Cameron, M.D., LoGrasso, P., Bannister, T. D., and Feng, Y., Bioorg. Med. Chem. Lett., 2011, vol. 21, pp. 1844–1848.

    Article  CAS  Google Scholar 

  21. Raju, A., Rajnikanth, S., Chandana, L.T.M., Rambabu, D., Krishna, G.R., Reddy, C.M., Girdhar Singh, D., Kishore, V.L.P., and Manojit, P., Chem. Commun., 2013, vol. 49, pp. 190–192.

    Article  Google Scholar 

  22. Baerfacker, L., PCT Int. Appl., 2010020366, 25 Feb 2010.

    Google Scholar 

  23. Abdel-Jalil, R.J., Wolfgang, V., and Muhammad, S., Tetrahedron Lett., 2004, vol. 45, pp. 3475–3476.

    Article  CAS  Google Scholar 

  24. Bakalovaa, S.M., Santosb, A.G., Timchevaa, I., Kanetia, J., Filipovaa, I.L., Dobrikova, G.M., and Dimitrova, V.D., J. Mol. Struc. (Theochem.), 2004, vol. 710, pp. 229–234.

    Article  Google Scholar 

  25. Repasky, M., Chandrasekhar, J., and Jorgensen, W., J. ComP.Chem., 2002, vol. 23, pp. 1601–1622.

    Article  CAS  Google Scholar 

  26. Kaviya, S., Santhanalakshmi, J., Viswanathan, B., Muthumary, J., and Srinivasan, K., Spectrochim. Acta Part A, 2011, vol. 79, pp. 594–598.

    Article  CAS  Google Scholar 

  27. Mert, S., Kasimogullari, R., Ica, T., Colak, F., Altun, A., and Ok, S., Eur. J. Med. Chem., 2014, vol. 78, pp. 86–96.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, University College of Science, Saifabad, Osmania University, Hyderabad, 500004, India

    P. Shankaraiah, S. Veeresham & A. K. D. Bhavani

Authors
  1. P. Shankaraiah
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. Veeresham
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. K. D. Bhavani
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. K. D. Bhavani.

Additional information

The text was submitted by the authors in English.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Shankaraiah, P., Veeresham, S. & Bhavani, A.K.D. Kumada cross coupling reaction based synthesis, antimicrobial and computational studies of 6-aryl-2-phenyl-3-methylquinazolin-4(3H)-ones. Russ J Gen Chem 86, 368–375 (2016). https://doi.org/10.1134/S1070363216020286

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363216020286

Keywords

Search

Navigation