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Synthesis and evaluation of novel isatin and 5-isatinylidenerhodanine-based furan derivatives as antibacterial agents

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Abstract

A simple synthesis of novel 5-isatinylidenerhodanine-based furan derivatives via a multi-component reaction is described. The reactive 1:1 intermediate, produced by the reaction of tert-butyl isocyanide and dialkyl acetylenedicarboxylates, was trapped at reflux temperature by acidic derivatives of isatin and 5-isatinylidenerhodanine to yield isatin and 5-isatinylidenerhodanine-based poly functionalized furan rings in fairly good yields. The products were analyzed for antibacterial activity against Gram-positive and Gram-negative bacteria. The results indicate that the synthesized compounds are effective against bacterial growth retardation activity to some extent and their effectiveness is higher for Escherichia coli.

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References

  1. V. Glover, J.M. Halaket, P.J. Watkins, A. Clone, B.L. Goodwin, M. Sandler, J. Neurochem. 51, 656 (1988)

    Article  CAS  Google Scholar 

  2. E.G. Mesropyran, G.B. Ambartsumyan, A.A. Avetisyan, M.G. Sarkisyan, G.S. Amazaspyan, Russ. J. Org. Chem. 37, 1476 (2001)

    Article  Google Scholar 

  3. S.K. Sridhar, M. Saravanan, A. Ramesh, Eur. J. Med. Chem. 36, 615 (2001)

    Article  CAS  Google Scholar 

  4. M. Sarangapani, V.M. Reddy, Indian. J. Pharm. Sci. 56, 174 (1994)

    Google Scholar 

  5. S.N. Pandeya, D. Sriram, G. Nath, E. De Clercq, Sci. Pharm. 67, 103 (1999)

    CAS  Google Scholar 

  6. S.N. Pandeya, D. Sriram, G. Nath, E. De Clercq, Pharm. Acta Helv. 74, 11 (1999)

    Article  CAS  Google Scholar 

  7. R.S. Varma, W.L. Nobles, J. Med. Chem. 10, 972 (1967)

    Article  CAS  Google Scholar 

  8. S.N. Pandeya, D. Sriram, G. Nath, E. De Clercq, Eur. J. Med. Chem. 35, 249 (2000)

    Article  CAS  Google Scholar 

  9. S.N. Pandeya, D. Sriram, G. Nath, E. De Clercq, Arzneimittel Forschun Drug Res. 50, 55 (2000)

    CAS  Google Scholar 

  10. N. Karal, A. Gürsoy, F. Kandemirli, N. Shvets, F.B. Kaynak, S. Özbey, V. Kovalishyn, V. Dimoglo, Bioorg. Med. Chem. 15, 5888 (2007)

    Article  Google Scholar 

  11. A.M. Melnick, A.D. Jr MacKerell, World Intellectual Property Organization WO Patent No. WO2008066887. Geneva, Switzerland: filed, (2008)

  12. Z. Zawahir, R. Dayam, J. Deng, C. Pereira, N. Neamati, J. Med. Chem. 52, 20 (2009)

    Article  CAS  Google Scholar 

  13. T.D. McKee, R.K. Suto, T. Tibbitts, J. Sowadski, World Intellectual Property Organization., WO Patent No. WO2004028535. Geneva, Switzerland: filed, (2004)

  14. R.T. Pardasani, P. Pardasani, D. Sherry, V. Chaturvedi, Ind. J. Chem. Sec. B 40, 1275 (2001)

    Google Scholar 

  15. V.I. Zapadnyuk, Vrachebnoe Delo (Kiev) 10, 71 (1966)

    Google Scholar 

  16. V.I. Zapadnyuk, Farmatsevticheskii Zhurnal (Kiev) 17, 36 (1962)

    Google Scholar 

  17. S.L. Gaonkar, H. Shimizu, Tetrahedron 66, 3314 (2010)

    Article  CAS  Google Scholar 

  18. S.M. Kupchan, M.A. Eakin, A.M. Thomas, J. Med. Chem. 101, 1147 (1971)

    Article  Google Scholar 

  19. M.M. Bandurraga, W. Fenical, S.F. Donovan, J. Clardy, J. Am. Chem. Soc. 104, 6463 (1982)

    Article  CAS  Google Scholar 

  20. G. Schulte, P.S. Scheuer, Helv. Chim. Acta 63, 2159 (1980)

    Article  CAS  Google Scholar 

  21. M. Hofnung, V.M. Quillardet, E. Touati, Res. Microbiol. 153, 427 (2002)

    Article  CAS  Google Scholar 

  22. M.W. Khan, M.J. Alam, M.A. Rashid, R. Chowdhury, Bioorg. Med. Chem. 13, 4796 (2005)

    Article  CAS  Google Scholar 

  23. R. Baharfar, S.M. Baghbanian, S.M. Vahdat, Tetrahedron Lett. 52, 6018 (2011)

    Article  CAS  Google Scholar 

  24. R. Baharfar, S.M. Baghbanian, J. Heterocycl. Chem. 49, 310 (2012)

    Article  CAS  Google Scholar 

  25. R. Baharfar, L. Jaffaari, R. Azimi, Chin. Chem. Lett. 22, 943 (2011)

    Article  CAS  Google Scholar 

  26. R. Baharfar, S.M. Baghbanian, Chin. Chem. Lett. 23, 6 (2012)

    Article  Google Scholar 

  27. A. Domling, Chem. Rev. 106, 17 (2006)

    Article  Google Scholar 

  28. A. Shaabani, A. Maleki, A.H. Rezayan, A. Sarvary, Mol. Divers. 15, 41 (2011)

    Article  CAS  Google Scholar 

  29. A. Domling, I. Ugi, Angew. Chem. Int. Ed. 39, 3168 (2000)

    Article  CAS  Google Scholar 

  30. R.B. Lesyk, B.S. Zimenkovsky, Org. Med. Chem. 8, 1547 (2004)

    CAS  Google Scholar 

  31. R. Bouhfid, N. Joly, F. Ohmani, E.M. Essassi, V. Lequart, J. Banoub, K. Kheddid, R. Carof, M. Massoui, P. Martin, Lett. Org. Chem. 5, 3 (2008)

    Article  CAS  Google Scholar 

  32. G. Schulte, P.S. Scheuer, Helv. Chim. Acta 63, 2159 (1980)

    Article  CAS  Google Scholar 

  33. F.C. Tenover, Encyclopedia of microbiology, 3rd edn. (Academic Press, Oxford, 2009), pp. 67–77

    Book  Google Scholar 

  34. M. Ghaemy, B. Aghakhani, M. Taghavi, S.M.A. Nasab, M. Mohseni, React. Funct. Polym. 73, 555 (2013)

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Chemistry, University of Mazandaran, 47416-95447, Babolsar, Iran

    Robabeh Baharfar, Sakineh Asghari & Somayeh Rassi

  2. Department of Microbiology, Faculty of Sciences, University of Mazandaran, Babolsar, Iran

    Mojtaba Mohseni

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  1. Robabeh Baharfar
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  2. Sakineh Asghari
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  3. Somayeh Rassi
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  4. Mojtaba Mohseni
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Correspondence to Robabeh Baharfar.

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Baharfar, R., Asghari, S., Rassi, S. et al. Synthesis and evaluation of novel isatin and 5-isatinylidenerhodanine-based furan derivatives as antibacterial agents. Res Chem Intermed 41, 6975–6984 (2015). https://doi.org/10.1007/s11164-014-1792-5

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  • DOI: https://doi.org/10.1007/s11164-014-1792-5

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