Skip to main content
SpringerLink
Log in

Synthesis, antimicrobial evaluation, and docking studies of some novel benzofuran based analogues of chalcone and 1,4-benzodiazepine

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

Abstract

A series of novel {5-[4-hydroxy-3-(4-phenyl-2,3-dihydro-1H-benzo[b][1,4]diazepin-2-yl)benzyl]- benzofuran-2-yl}(phenyl)methanones (5a–5g) were prepared by the condensation of (E)-3-{5-[(2- benzoylbenzofuran-5-yl)methyl]-2-hydroxyphenyl}-1-phenylprop-2-en-1-one (chalcone) (4a) with various substituted o-phenylene diamines in the presence of oxalic acid as catalyst. The structures of all compounds were characterized by FTIR, 1H NMR, 13C NMR, and MS. The representative examples were screened in vitro for antimicrobial activity. Among all compounds 4g and 5g showed potent antibacterial activity, 4b and 5g showed good antifungal activity. The data was further compared with structure based investigations using docking studies with the crystal structure of adenosine-5'-(β,γ-imido)triphosphate (2ONJ) from Staphylococcus aureus for antibacterial activity and trypsin (1FY5) protein from Fusarium oxysporum for the antifungal activity. The score values estimated by genetic algorithm were found to have a good correlation with the experimental inhibitory potencies.

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. Xue-Quan Wang, Lan-Xiang Liu, Yan Li, Cheng-Jun Sun, Wen Chen, Liang Li, Hong-Bin Zhang, Xiao-Dong Yang, Eur. J. Med. Chem., 2013, vol. 62, pp 111. DOI: 10.1016/j.ejmech.2012.12.040.

    Article  Google Scholar 

  2. Yuhong, J.U. and Varma, R.S.J., J. Org. Chem., 2006, vol. 71, p. 135. DOI: 10.1021/jo051878h.

    Article  Google Scholar 

  3. Sarma, B.K., Mishra, P.K., Singhai, P.K., and Singh, U.P., Mycobiology., 2007, vol. 35, p. 72. DOI: 10.4489/MYCO.2007.35.2.072.

    Article  Google Scholar 

  4. Parikh, K.S. and Joshi, D.S., Med. Chem. Res., 2013, vol. 22, p. 3688. DOI: 10.1007/s004412-0369-3.

    Article  CAS  Google Scholar 

  5. Dimmock, J.R., Ellas, D.W., Beazely, M.A., and Kandepu, N.M., Curr. Med. Chem., 1999, vol. 6(12), p. 1125.

    CAS  Google Scholar 

  6. De Meyer, N., Haemers, A., Mishra, L., Pandey, H.K., Peters, L.A., Vanden Berghe, D.A., and Vlietinck, A.J., J. Med. Chem., 1991, vol. 34, p. 736. DOI: 10.1021/jm00106a700.

    Article  Google Scholar 

  7. Ducki, S., Forrest, R., Hadfield. J., Kendall, A., Lawerence, N.J., McGrown, A.T., and Rennison, D., Bioorg. Med. Chem. Lett., 1998 vol. 8, p. 1051. DOI: DOI: 10.1016/S0960-894X (98)00162-0.

    Article  CAS  Google Scholar 

  8. Mei-Lin, Go., Liu Mei., Wilairat, P., Rosenthal, P.J., Saliba, K.J., and Kirk, K., Antimicrob Agents Chemother., 2004, vol. 48, p. 3241. DOI: 10.1128/AAC.48.9.3241-3245.2004.

    Article  Google Scholar 

  9. Azam, A., Hayat, F., Mosely, E., Attar, S., and Vanzyl, R., Eur. J. Med. Chem., 2011, vol. 46, p. 1897. DOI: 10.1016/j.ejmech.2011.02.004.

    Article  Google Scholar 

  10. Satyanarayana, M., Tiwari, P., Tripathi, B.K., Srivastava, A.K., and Pratap, R., Bioorg. Med. Chem., 2004, vol. 12, p. 883. DOI: 10.1016/j.bmc.2003.12.026.

    Article  CAS  Google Scholar 

  11. Padhyee, S., Ahmad, A., Oswal, N., and Sarkar, F.H., J. Hematol. Oncol., 2009, vol. 2, p. 38. DOI: 10.1186/1756-8722-2-38.

    Article  Google Scholar 

  12. Iwalewa, E.O., Oyedapo, O.A., Adewunmi, C.O., and Makunja, V.O., J. Biol. Sci., 2008, vol. 8, p. 131. DOI: 10.3923/jbs.2008.131.136.

    Article  Google Scholar 

  13. Nam, N.H., Kim, Y., You, Y.J., Hong, D.H., Kim, H.M., and Ahn, B.Z., Eur. J. Med. Chem., 2003, vol. 38, p. 179. DOI: 10.1016/S0223-5234(02)01443-5.

    Article  CAS  Google Scholar 

  14. Dimmock, J.R., Ellas, D.W., Beazely, M.A., and Kandepu, N.M., Curr. Med. Chem., 1999, vol. 6, p. 1125.

    CAS  Google Scholar 

  15. Khan, M.W., Alam, M.J., Rashid, M.A., and Chowdhury, R. A., Bioorganic & Medicinal Chemistry., 2005, vol. 13, p. 4796. DOI: 10.1016/j.bmc.2005.05.009.

    Article  CAS  Google Scholar 

  16. Buu-Hoi, N.P., Bisagni, E., Royer, R., and Routier, C., J. Chem. Soc., 1957, p. 625. DOI: 10.1039/JR9570000625.

    Google Scholar 

  17. Buu-Hoi, N., Saint-Ruf, G., Loc, T.B., and Xuong, N.D., J. Chem. Soc., 1957, p. 2593. DOI: 10.1039/JR9570002593.

    Google Scholar 

  18. Benkli, K., Gundogdu-Karaburun, N., Karaburun, A.C., Ucucu, U., Demirayak, S., and Kiraz, N., Eur. J. Med. Chem., 2006, vol. 41, p. 651. DOI: 10.1016/j.ejmech.2005.12.013.

    Article  Google Scholar 

  19. Baraldi, P.G., Romagnoli, R., Beria, I., Geroni, P.C., Mongelli, N., Bianchi, N., Mischiati, C., and Gambari, R., J. Med. Chem., 2000, vol. 43, p. 2675. DOI: 10.1021/jm9911229.

    Article  CAS  Google Scholar 

  20. Chandrashekar. A., Eswarappa, B., Yadav, D.B., Venkatesh, K.B., Raghu, N., and Shivakumar, M.C., Med. Chem. Res., 2013, vol. 22, p. 78. DOI: 10.1007/s00044012-0017-y.

    Article  Google Scholar 

  21. Middlemiss, D., Drew, G.M., Ross, B.C., Robertson, M.J., Scopes, D.C., Dowle, M. D., Hamblett, J., Cardwell, K., Clark, K. L., Coote, S., Eldred, C.D., Hamblett, J., Hilditch, A., Hirst, G.C., Jack, T., Montona, J., Panchal, T.A., Paton, S.M., Shah, P., Stuart, G., and Travers, A., Bio. Med. Chem. Lett., 1991, vol. 1, p. 711. DOI: 10.1016/S0960-894X(01)81053-2.

    Article  CAS  Google Scholar 

  22. Leung, A.Y. and Foster, S.W., Encyclopedia of Common Natural Ingredients Used in Food, Drugs, and Cosmetics, New York: Wiley, 1996, vol. 35, p. 648.

    Google Scholar 

  23. Elvers, B., Hawkins, S., and Schulz, G., Optical Brighteners, Weinheim: VCH, 1999, vol. A18, p. 153, 5 ed.

    Google Scholar 

  24. Antoine, M., Barreu, M., Desconclois, J.F., Girard, P., and Picaut, G., Chem. Abstr., 1991, vol. 114, p. 14339.

    Google Scholar 

  25. Kusanur, R., Ghate, M., and Kulkurani, M., J. Chem. Sci., 2004, vol. 116, p. 265. DOI: 10.1007/BF02708277.

    Article  CAS  Google Scholar 

  26. Basawaraj, R., Naubade, K., and Sangapure, S.S., Indian. J. Heterocycl. Chem., 2008, vol. 17, p. 217.

    CAS  Google Scholar 

  27. Grossi, G., Braccio, M.D., and Calcina, F., Eur. J. Med. Chem., 2002, vol. 37, p. 933. DOI: 10.1016/S0223-5234 (02)01400-9.

    Article  CAS  Google Scholar 

  28. Kusanur, A.R., Ghate, M., and Kulkarni, V.M., J. Chem. Sci., 2004, vol. 11, p. 265. DOI: 10.1007/BF02708277.

    Article  Google Scholar 

  29. Jauhari, P.K., Bhavani, A., Varalwar, S., Singhal, K., Raj, P., Med. Chem. Res., 2008, vol. 17, p. 412. DOI: 10.1007/s00044-007-9076-x.

    Article  CAS  Google Scholar 

  30. Mahajan, A., Kumar, V., Mansour, N.R.N., Bickle, Q., and Chibale, K., Bioorg. Med. Chem. Lett., 2008, vol. 18, p. 2333. DOI: 10.1016/j.bmcl.2008.02.077.

    Article  CAS  Google Scholar 

  31. Drabu, S. and Kumar, N., Asian. J. Chem., 2007, vol. 19, p. 5743.

    CAS  Google Scholar 

  32. Fred, E.D., Byung, H.L., Sandra, S.J., and Eileen, M.C., J. Med. Chem., 2003, vol. 46, p. 2057. DOI: 10.1021/jm020482k.

    Article  Google Scholar 

  33. Gandhi, M. and Olyaei, A., J. Het. Chem., 2007, vol. 44, p. 323. DOI: 10.1002/jhet.5570440207.

    Article  Google Scholar 

  34. Jadhav, S.B., Shasthri, R.A., Bagul, K.R., and Gaikwad, K.V., Indian. J. Het. Chem., 2009, vol. 18, p. 319. DOI: 10.9790/5736-09227175.

    CAS  Google Scholar 

  35. Marvel, C.S. and Tarkoy, N.J., Am. Chem. Soc., 1957, vol. 79, p. 6000. DOI: 10.1021/ja01579a041.

    Article  CAS  Google Scholar 

  36. Thool, A.W. and Ghiya, B.J.J., Indian Chem. Soc., 1988, vol. 65, p. 522.

    CAS  Google Scholar 

  37. Aniket, P.S., Jaiprakashn, S., Nanasahe, B.B.D., Ajinkya, P.S., Paravani, S.W., and Devanand, B.S., J. Chil. Chem. Soc., 2013, vol. 58, p. N4. DOI: 10.4067/S0717-97072013000400064.

    Google Scholar 

  38. Bhavanarushi, S., Kanakaiah, V., Gandu, B., Gangagnirao, A., and Vatsala, R., Med. Chem. Res., 2014, vol. 23(1), p. 158. DOI: 10.1007/s00044-013-0623-3.

    Article  CAS  Google Scholar 

  39. Patel, M.A., Bhila, V.G., Patel, N.H., Patel, A.K., and Brahmbhatt, D.I., Med. Chem. Res., 2012, vol. 21, p. 4381. DOI: 10.1007/s00044-012-9978-0.

    Article  CAS  Google Scholar 

  40. Keche, A.P., Hatnapure, G.D., Tale, R.T., Rodge, A.H., Birajdar, S.S., and Kamble, V.M., Med. Chem. Res., 2013, vol. 22, p. 1480. DOI: 10.1007/s00044-012-0144-5.

    Article  CAS  Google Scholar 

  41. Jones, G. and Willett, P., Glen, R.C., J. Mol. Biol., 1995, vol. 43, p. 245. DOI: 10.1016/S0022-2836(95) 80037-9.

    Google Scholar 

  42. Verdonk, M.L., Cole, J.C., Hartshorn, M.J., Murray, C.W., and Taylor, R.D., Struct. Funct. Bioinform., 2003, vol. 52, p. 609. DOI: 10.1002/prot.10465.

    Article  CAS  Google Scholar 

  43. Trott, O. and Olson, A.J., J. Comp. Chem., 2010, vol. 31, p. 455. DOI: 10.1002/jcc.21334.

    CAS  Google Scholar 

  44. Dawson, R.J.P. and Locher, K.P., FEBS Lett., 2007, vol. 581, p. 935. DOI: 10.1016/j.febslet.2007.01.073.

    Article  CAS  Google Scholar 

  45. Rypniewski, W.R., Ostergaard, P.R., Norregaard-Madsen, M., Dauter, M., and Wilson, K.S., Acta Crystallogr., Sect. D, 2001, vol. 57, p. 8. DOI: 10.1107/S0907444900014116.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

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

    B. Shankar, P. Jalapathi, M. Ramesh, A. Kishore Kumar & M. Ragavender

  2. Bioengineering and Environmental Sciences, Indian Institute of Chemical Technology, Hyderabad, 500007, India

    G. Bharath

Authors
  1. B. Shankar
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. P. Jalapathi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. Ramesh
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. Kishore Kumar
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. M. Ragavender
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. G. Bharath
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to P. Jalapathi.

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

Shankar, B., Jalapathi, P., Ramesh, M. et al. Synthesis, antimicrobial evaluation, and docking studies of some novel benzofuran based analogues of chalcone and 1,4-benzodiazepine. Russ J Gen Chem 86, 1711–1721 (2016). https://doi.org/10.1134/S107036321607029X

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S107036321607029X

Keywords

Search

Navigation