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Synthesis, characterization and in vitro antibacterial evaluation of 1-(7,7-dimethyl-2-morpholino-5,6,7,8-tetrahydroquinazolin-4-yl)piperidine-4-carboxamide derivatives

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Abstract

A series of six novel 1-(7,7-dimethyl-2-morpholino-5,6,7,8-tetrahydroquinazolin-4-yl)piperidine-4-carboxamide derivatives has been synthesized and characterized using various spectral techniques (1H and 13C NMR, LCMS, IR). The antibacterial activities of these compounds have been screened against nine different Gram-positive and Gram-negative bacterial strains. The results show that quinazoline derivatives containing thiazole ring 2a and 2b exhibit good antibacterial activity amongst the compounds under investigation.

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References

  1. A.R. Katritzky, C.W. Rees, J.D Hepworth (eds.), Comprehensive Heterocyclic Chemistry, vol. 3 (Pergamon Press, Oxford, 1985), p. 150

  2. J.A. Joule, K. Mills, Heterocyclic Chemistry (Wiley, New York, 2008)

    Google Scholar 

  3. J.D. Hepworth, C.D. Gabbutt, B.M. Heron (eds.), Comprehensive Heterocyclic Chemistry, vol. 5 (Pergamon Press, Oxford, 1995), p. 221

  4. R.E. Looper, M.T.C. Runnegar, R.M. Williams, Angew. Chem. Int. Ed. 44, 3874 (2005)

    Article  Google Scholar 

  5. J. Kobayashi, F. Kanda, M. Ishibashi, H. Shigemori, J. Org. Chem. 56, 4574 (1991)

    Article  CAS  Google Scholar 

  6. G.S. Skinner, P.R. Wunz, J. Am. Chem. Soc. 73, 3814 (1951)

    Article  CAS  Google Scholar 

  7. G. Noronha, J. Cao, C. Gritzen, C. Mak, A. McPherson, V.P. Pathak, J. Renick, R.M. Soll, B. Zeng, E. Dneprovskaia, U.S. Patent 0027070 (2008)

  8. J.D. Charrier, E.O. Michael, U.S. Patent 0159749 (2016)

  9. A.B. Siddiqui, A.R. Trivedi, V.B. Kataria, V.H. Shah, Bioorg. Med. Chem. Lett. 24, 1493 (2014)

    Article  CAS  Google Scholar 

  10. V. Goudar, P. Rashmi, U. Shantharam, K. Hazra, L.G. Nargund, J. Chem. Pharm. Res. 6, 3100 (2012)

    Google Scholar 

  11. K. Gullapelli, M.K. Thupurani, Z. Brahmeshwari, Int. J. Pharm. Biol. Sci. 5, 682 (2014)

    CAS  Google Scholar 

  12. O.A. Fathalla, F. Zeid, M.E. Haiba, M. Soliman, H.I. Abd-Elmoez, W.S. El-Serwy, World J. Chem. 4, 127 (2009)

    CAS  Google Scholar 

  13. C. Cano, K. Saravanan, C. Bailey, J. Bardos, N.J. Curtin, M. Frigerio, B.T. Golding, I.R. Hardcastle, M.G. Hummersone, K.A. Menear, D.R. Newell, C.J. Richardson, K. Shea, G.C.M. Smith, P. Thommes, A. Ting, R.J. Griffin, J. Med. Chem. 56, 6386 (2013)

    Article  CAS  Google Scholar 

  14. C. Cano, O.R. Barbeau, C. Bailey, X.L. Cockcroft, N.J. Curtin, H. Duggan, M. Frigerio, B.T. Golding, I.R. Hardcastle, M.G. Hummersone, C. Knights, K.A. Menear, D.R. Newell, C.J. Richardson, G.C.M. Smith, B. Spittle, R.J. Griffin, J. Med. Chem. 53, 8498 (2010)

    Article  CAS  Google Scholar 

  15. I. Chuckowree, A. Folkes, S. Oxenford, A. Olivero, D.P. Sutherlin, Z. Bing-Yan, WO 066084 A1 (2009)

  16. T. Sekiya, H. Hiranuma, T. Kanayama, S. Hata, Eur. J. Med. Chem. 15, 317 (1980)

    CAS  Google Scholar 

  17. T. Chou, K. Li, K.J. Frankowski, F.J. Schoenen, R.J. Deshaies, Chem. Med. Chem. 8, 297 (2013)

    Article  CAS  Google Scholar 

  18. D. Dibyendu, I.K. Khanna, S. Pillarisetti, WO028174 A1 (2010)

  19. N.R. Norcross, B. Baragaña, C. Wilson, I. Hallyburton, M. Osuna-Cabello, S. Norval, J. Riley, L. Stojanovski, F.R.C. Simeons, A. Porzelle, R. Grimaldi, S. Wittlin, S. Duffy, V.M. Avery, S. Meister, L. Sanz, B. Jiménez-Díaz, I. Angulo-Barturen, S. Ferrer, M.S. Martínez, F.J. Gamo, J.A. Frearson, D.W. Gray, A.H. Fairlamb, E.A. Winzeler, D. Waterson, S.F. Campbell, P. Willis, K.D. Read, I.H. Gilbert, J. Med. Chem. 59, 6101 (2016)

    Article  CAS  Google Scholar 

  20. J.R. Koenig, H. Liu, I. Drizin, D.G. Witte, T.L. Carr, A.M. Manelli, I. Milicic, M.I. Strakhova, T.R. Miller, T.A. Esbenshade, J.D. Brioni, M. Cowart, Bioorg. Med. Chem. Lett. 20, 1900 (2010)

    Article  CAS  Google Scholar 

  21. Y. Chen, G. Wang, X. Xu, B. Liu, J. Li, G. Zhang, Molecules 16, 5785 (2011)

    Article  CAS  Google Scholar 

  22. F. Rahim, H. Ullah, M.T. Javid, A. Wadood, M. Taha, M. Ashraf, A. Shaukat, M. Junaid, S. Hussain, W. Rehman, Bioorg. Chem. 62, 15 (2015)

    Article  CAS  Google Scholar 

  23. F. Rahim, M.T. Javed, H. Ullah, A. Wadood, M. Taha, M. Ashraf, Q. Ain, M.A. Khan, F. Khan, S. Mirza, K.M. Khan, Bioorg. Chem. 62, 106 (2015)

    Article  CAS  Google Scholar 

  24. S.G. Kucukguzel, A. Mazi, F. Sahin, S. Ozturk, J. Stables, Eur. J. Med. Chem. 38, 1005 (2003)

    Article  CAS  Google Scholar 

  25. Y.K. Kang, K.J. Shin, K.H. Yoo, K.J. Seo, C.Y. Hong, C. Lee, S.Y. Park, D.J. Kim, S.W. Park, Bioorg. Med. Chem. Lett. 10, 95 (2000)

    Article  CAS  Google Scholar 

  26. S. Tetsuo, H. Hidetoshi, U. Masayuki, H. Shunsuke, Y. Shun-Ichi, Chem. Pharm. Bull. 29, 948 (1981)

    Article  Google Scholar 

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Acknowledgement

One of the authors (BS) is grateful to the Management, Anthem Biosciences, Bangalore, India, for their invaluable support and allocation of resources for this work. He wishes to thank the Analytical Chemistry team of Anthem Biosciences for carrying out all the analytical work. Also, the help of the Discovery Biology team of Anthem Biosciences is greatly acknowledged for executing anti-bacterial studies.

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Authors and Affiliations

  1. Anthem Biosciences Private Limited, Bangalore, 560 099, India

    Balaraman Selvakumar

  2. Department of Chemistry, Gandhigram Rural Institute (Deemed University), Gandhigram, 624 302, India

    Balaraman Selvakumar & Kuppanagounder P. Elango

Authors
  1. Balaraman Selvakumar
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  2. Kuppanagounder P. Elango
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Correspondence to Kuppanagounder P. Elango.

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Selvakumar, B., Elango, K.P. Synthesis, characterization and in vitro antibacterial evaluation of 1-(7,7-dimethyl-2-morpholino-5,6,7,8-tetrahydroquinazolin-4-yl)piperidine-4-carboxamide derivatives. Res Chem Intermed 43, 5535–5546 (2017). https://doi.org/10.1007/s11164-017-2945-0

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