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Morpholino pyrimidinyl acetamides: design, green chemical one-pot synthesis, and in vitro microbiological evaluation

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Pharmaceutical Chemistry Journal Aims and scope

A green chemical “one-pot” reaction procedure for the synthesis of a series of novel morpholino pyrimidinyl acetamides (19 – 27) under microwave irradiation in dry medium has been developed. The synthesized compounds are characterized by the melting point, elemental analysis, mass spectrometry, FT-IR spectroscopy, and one-dimensional NMR (1H and 13C) spectroscopic data. All the synthesized compounds have been screened for their in vitro antibacterial and antifungal activities against clinically isolated bacterial strains of Bacillus subtilis, Bacillus cerues, Micrococcus luteus, Salmonella typhii, Shigella felxneri and fungal strains of Aspergillus niger, Candida albicans, Candida 6 and Candida 51 and the results are discussed.

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References

  1. C. O. Kappe, Angew. Chem. Int. Ed. 43, 6250 (2004).

    Article  CAS  Google Scholar 

  2. P. Lidstrom, J. P. Tierney, B. Wathey, and J. Westman, Microwave-Assisted Organic Synthesis Eds.; Blackwell: Oxford, (2005).

  3. A. Loupy, Microwaves in Organic Synthesis; Ed.; Wiley-VCH: Weinheim, (2006).

  4. E. Ashry and A. A. Kassem, ARKIVOC, 9, 1 (2006)

    Google Scholar 

  5. N. E. Leadbeater and J. R. Schmink. Tetrahedron, 63, 6764 (2007).

    Article  CAS  Google Scholar 

  6. F. L. Mercer, T. E. Lindhorst and B. Commoner, Science, 117, 558 (1953).

    Article  PubMed  CAS  Google Scholar 

  7. G. Matolesy, World Rev. Pest. Contr. 10, 50 (1971).

    Google Scholar 

  8. R. E. Weishaar, M. C. Cain and J. A. Bristor, J. Med. Chem. 1999, 42, 805–818.

    Article  Google Scholar 

  9. B. Commoner and F. L. Mercer, Nature, 168, 113 (1951).

    Article  PubMed  CAS  Google Scholar 

  10. V. J. Ram, V. K. Singha and P. Guru, Eur. J. Med. Chem. 25, 549 (1990)

    Article  Google Scholar 

  11. V. K. Ahluwalia, A. Chauhan and A. Khurana, Indian J. Chem. 28B, 964 (1989).

    CAS  Google Scholar 

  12. S. W. Tam, Y. N. Wong, S. Huang and H. Shen, Eur. J. Med. Chem. 42, 809 (1999).

    Google Scholar 

  13. R. N. Goyal, R. Bhusan and A. Agarwal, J. Indian Chem. Soc. 62, 229 (1985).

    CAS  Google Scholar 

  14. D. J. Hamilton and A. Sutherland, Tetrahedron Lett. 45, 5739 (2004).

    Article  CAS  Google Scholar 

  15. S. Akyuz, and T. Akyuz, J. Mol. Struct. 744, 881, (2005).

    Article  Google Scholar 

  16. S. Akyuz, J. Mol. Struct. 651, 205, (2003).

    Article  Google Scholar 

  17. D. Chauhan, J. S. Chauhan and J. Singh, Indian J. Chem. 40B, 524 (2001).

    CAS  Google Scholar 

  18. S. Kushner, R. T. Cassell, J. Morton and J. H. William, J. Org. Chem. 16, 1283 (1951).

    Article  CAS  Google Scholar 

  19. N. K. Kochetkov, and N. V. Dudykina, J. Gen. Chem. USSR, 26, 2915 (1951).

    Google Scholar 

  20. N. K. Kochetkov, and N. V. Dudykina, J. Gen. Chem. USSR, 32, 1481 (1957)

    Google Scholar 

  21. G. B. Eregowda, H. N. Kalpana, R. Hedge and K. N. Thimmaiah, Indian J. Chem. 39B, 243 (2000)

    CAS  Google Scholar 

  22. M. A. Al-Haiza, M. S. Mostafa and M. Y. El-Kady, Molecules, 8, 275 (2003).

    Article  CAS  Google Scholar 

  23. J. Gan, Q. Wang, S. R. Yates, C. Koskinen, and W. A. Jury, Proc. Natl. Acad. Sci. U. S. A. 99, 5189 (2002).

    Article  PubMed  CAS  Google Scholar 

  24. S. J. Hasan, V. S. Bhakar Rao, S. Husain and P. B. Sattur, Indian J. Chem. 9, 1022 (1971).

    CAS  Google Scholar 

  25. K. Marouka, and H. Yamamoto, Comprehensive Organic Synthesis, B. M. Trost, Pergamonn Press, 6, 6221 (1991)

  26. R. Manfred, M. Michael, S. Robert and G. Wolfgang, Eur. Pat. Appl. EP 334146, 28 (1989) Chem. Abstr. 112, 178999 (1989)

    Google Scholar 

  27. R. Manfred, M. Michael, S. Robert, G. Wolfgang and R. Eckhard, Ger. Offen. DE 3729285, 17 (1989). Chem. Abstr. 111, 134172 (1989).

    Google Scholar 

  28. J. J. Hale, S. G. Mills, M. MacCross, C. P. Dorn, P. E. Fink, R. J. Budhu, R. A. Reamer, W. P. Huskey, D. Luffer-Atlas, B. J. Dean, E. M. McGowan, W. P. Feeney, S. H. L. Chiu, M. A. Cascieri, G. G. Chicchi, M. M. Kurtz, S. Sadowski, E. Ber, F. D. Tattersall, N. M. J. Rupniak, A. R. Williams, W. Raycroft, R. Hargreaves, J. M. Metzger and D. E. Maclntyre, J. Med. Chem. 43, 1234 (2000).

    Article  PubMed  CAS  Google Scholar 

  29. C. P. Dorn, J. J. Hale, M. MacCoss and S. G. Mills, US Patent 5691336, 82 (1997). Chem. Abstr. 128, 48231 (1997)

  30. M. H. Fisher and M. J. Wyvratt, U. S. Patent 5077290:10 (1991). Chem. Abstr. 116, 214513 (1991)

    Google Scholar 

  31. P. Avramova, N. Danchev, R. Buyukliev and T. Bogoslovova, Arch. Pharm. (Weinheim, Ger.) 331, 342 (1998).

    Article  CAS  Google Scholar 

  32. Lutz F. Tietze and Nils Rackelmann, Pure Appl. Chem., 76, 1967 (2004).

    Article  CAS  Google Scholar 

  33. M. Gopalakrishnan, P. Sureshkumar, J. Thanusu, C. Prabhu and V. Kanagarajan, J. Chem. Res. 2007, 2, 80 (2007).

    Article  Google Scholar 

  34. M. Gopalakrishnan, P. Sureshkumar, V. Kanagarajan, J. Thanusu and Govindaraju R., J. Chem. Res., 5, 299 (2005).

    Article  Google Scholar 

  35. M. Gopalakrishnan, J. Thanusu and V. Kanagarajan, J. of Korean Chem. Soc., 52, 47 (2008).

    Article  CAS  Google Scholar 

  36. M. Gopalakrishnan, V. Kanagarajan and J. Thanusu, Green Chem. Lett. 1, 241 (2008).

    Article  CAS  Google Scholar 

  37. M. Gopalakrishnan, P. Sureshkumar, V. Kanagarajan and J. Thanusu, J. Korean Chem. Soc., 51, 346 (2007).

    Article  CAS  Google Scholar 

  38. S. Kothari, M. Singhal, D. Vijayvergia, R. Vyas and B. L. Verma, J. Indian Chem. Soc., 77, 329 (2000).

    CAS  Google Scholar 

  39. A. J. Speziale and P. C. Hamm, J. Am. Chem. Soc., 78, 2556 (1956).

    Article  CAS  Google Scholar 

  40. M. H. Dhar, M. M. Dhar, B. N. Dhawan, B. N. Mehrotra, C. Ray, Indian J. Exp. Biol., 6, 232 (1968).

    PubMed  CAS  Google Scholar 

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Acknowledgements

Authors are thankful to the NMR Research Centre (Indian Institute of Science, Bangalore) for recording spectra. One of the authors (V. K.) is grateful to the Council of Scientific and Industrial Research (CSIR, New Delhi, Republic of India) for providing financial support in the form of CSIR-Senior Research Fellowship (SRF) in Organic Chemistry.

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  1. Synthetic Organic Chemistry Laboratory, Department of Chemistry, Annamalai University, Annamalainagar-608 002, Tamil Nadu, India

    V. Kanagarajan & M. Gopalakrishnan

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  1. V. Kanagarajan
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  2. M. Gopalakrishnan
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Correspondence to M. Gopalakrishnan.

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Kanagarajan, V., Gopalakrishnan, M. Morpholino pyrimidinyl acetamides: design, green chemical one-pot synthesis, and in vitro microbiological evaluation. Pharm Chem J 45, 170–177 (2011). https://doi.org/10.1007/s11094-011-0586-y

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