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Highly functionalized pyranopyrazoles: synthesis, antimicrobial activity, simulation studies and their structure activity relationships (SARs)

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Abstract

Development of potent antibacterial and antifungal agents is a permanently new and unremitting investigation in the therapeutic field. Still, medicinal research wants to find the best antimicrobial agent. To attain this goal , here, the present work synthesis, simulation, and antimicrobial studies of pyranopyrazole derivatives were discussed. Among the reported compounds, 4b has dominant antimicrobial activity that was due to its higher dipole moment. Also, this compound has the most hydrophilic nature and low Eg value. Besides, compound 4e has the next higher dipole moment, hydrophilic property and efficient biological activity. The rationale of these results explained that the comparison of electronic results with biological data is the better way to find the potent pharmaceutical drug compounds.

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References

  1. M.A. Fischbach, C.T. Walsh, Science 325, 1089 (2009)

    Article  CAS  Google Scholar 

  2. G.J. Armelagos, P.J. Brown, B. Turner, Soc. Sci. Med. 61, 755 (2005)

    Article  Google Scholar 

  3. A.H. Shamroukh, M.E.A. Zaki, E.M.H. Morsy, F.M. Abdel-Motti, F.M.E. Abdel-Megeid, Arch. Pharm. Chem. Life Sci. 340, 345 (2007)

    Article  CAS  Google Scholar 

  4. M.D. Aytemir, U. Calis, M. Ozalp, Arch. Pharm. Chem. Life Sci. 337, 281 (2004)

    Article  CAS  Google Scholar 

  5. F. Chabchoub, M. Messaad, H.B. Mansour, L. Chekir-Ghedira, M. Salem, Eur. J. Med. Chem. 42, 715 (2007)

    Article  CAS  Google Scholar 

  6. T.B. Prakash, G.D. Reddy, A. Padmaja, V. Padmavathi, Eur. J. Med. Chem. 82, 347 (2014)

    Article  Google Scholar 

  7. G.M. Reddy, P.R. Reddy, V. Padmavathi, A. Padmaja, Arch. Pharm. Chem. Life Sci. 346, 154 (2013)

    Article  Google Scholar 

  8. G.M. Reddy, A. Muralikrishna, V. Padmavathi, A. Padmaja, T.K. Tilak, C.A. Rao, Chem. Pharm. Bull. 61, 1291 (2013)

    Article  CAS  Google Scholar 

  9. G. Bertuzzi, E. Locatelli, D. Colecchia, P. Calandro, B.F. Bonini, J.Z. Chandanshive, A. Mazzanti, P. Zani, M. Chiariello, M. Comes, Franchini. Eur. J. Med. Chem. 117, 1 (2016)

    Article  CAS  Google Scholar 

  10. M.F. Khan, M.M. Alam, G. Verma, W. Akhtar, M. Akhter, M. Shaquiquzzaman, Eur. J. Med. Chem. 120, 170 (2016)

    Article  CAS  Google Scholar 

  11. G. Vasuki, K. Kumaravel, Tetrahedron Lett. 49, 5636 (2008)

    Article  CAS  Google Scholar 

  12. J.L. Wang, D. Liu, Z.J. Zhang, S. Shan, X.S.M. Srinivasula, C.M. Croce, E.S. Alnemri, Z. Huang, Proc. Natl. Acad. Sci. U.S.A. 97, 7124 (2000)

    Article  CAS  Google Scholar 

  13. E.S. El-Tamany, F.A. El-Shahed, B.H. Mohamed, J. Serb. Chem. Soc. 64, 9 (1999)

    CAS  Google Scholar 

  14. Z.H. Ismail, G.M. Aly, M.S. El-Degwi, H.I. Heiba, M.M. Ghorab, Egypt. J. Biotechnol. 13, 73 (2003)

    CAS  Google Scholar 

  15. M.E.A. Zaki, H.A. Soliman, O.A. Hiekal, A.E. Rashad, Sect. C J. Biosci. 61, 1 (2006)

    CAS  Google Scholar 

  16. S.C. Kuo, L.J. Huang, H. Nakamura, J. Med. Chem. 27, 539 (1984)

    Article  CAS  Google Scholar 

  17. L. Bonsignore, G. Loy, D. Secci, A. Calignano, Eur. J. Med. Chem. 28, 51 (1993)

    Article  Google Scholar 

  18. H. Wamhoff, E. Kroth, C. Strauch, Synthesis 11, 1129 (1993)

    Article  CAS  Google Scholar 

  19. S.R. Mandha, S. Siliveri, M. Alla, V.R. Bommena, M.R. Bommineni, S. Balasubramanian, Bioorg. Med. Chem. Lett. 22, 5272 (2012)

    Article  CAS  Google Scholar 

  20. M. Mamaghani, R.H. Nia, F. Shirini, K. Tabatabaeian, M. Rassa, Med. Chem. Res. 24, 1916 (2015)

    Article  CAS  Google Scholar 

  21. X.H. Yang, P.H. Zhang, Z.M. Wang, F. Jing, Y.H. Zhou, L.H. Hu, Ind. Crops Prod. 52, 413 (2014)

    Article  CAS  Google Scholar 

  22. M.H. Helal, S.A. El-Awdan, M.A. Salem, T.A. Abd-elaziz, Y.A. Moahamed, A.A. El-Sherif, G.A.M. Mohamed, SpectrochimicaActa Part A: Mol Biomol Spectrosc 135, 764 (2015)

    Article  CAS  Google Scholar 

  23. Z. Yan, A. Liu, M. Huang, M. Liu, H. Pei, L. Huang, H. Yi, W. Liu, A. Hu, Eur. J. Med. Chem. 149, 170 (2018)

    Article  CAS  Google Scholar 

  24. P. Politzer, J.S. Murray, Z. Peralta-Inga, Int. J. Quantum Chem. 85, 676 (2001)

    Article  CAS  Google Scholar 

  25. P. Politzer, J.S. Murray, M.C. Concha, Int. J. Quantum Chem. 88, 19 (2002)

    Article  CAS  Google Scholar 

  26. S.P. Gejji, C.H. Suresh, K. Babu, S.R. Gadre, J. Phys. Chem. 103, 7474 (1999)

    Article  CAS  Google Scholar 

  27. J. Tomasi, R. Bonaccorsi, R. Cammi, in Theoretical Models of Chemical Bonding, ed. by R. Maksic (Springer, Berlin, 1990)

    Google Scholar 

  28. X.H. Liu, Y.M. Fang, F. Xie, R.R. Zhang, Z.H. Shen, C.X. Tan, J.Q. Weng, T.M. Xu, H.Y. Huang, Pest Manag. Sci. 73, 1900 (2017)

    Article  CAS  Google Scholar 

  29. X.H. Liu, Q. Wang, Z.H. Sun, D.E. Wedge, J.J. Becnel, A.S. Estep, C.X. Tan, J.Q. Weng, Pest Manag. Sci. 73, 953 (2017)

    Article  CAS  Google Scholar 

  30. X.M. Ding, Z.W. Zhai, L.P. Lv, Z.H. Sun, X.H. Liu, Front. Chem. Sci. Eng. 11, 379 (2017)

    Article  CAS  Google Scholar 

  31. A.K. Bhattacharrjee, J.M. Karle, Bioorg. Med. Chem. 6, 1927 (1998)

    Article  Google Scholar 

  32. A.K. Bhattacharrjee, J.M. Karle, Chem. Res. Toxicol. 12, 422 (1999)

    Article  Google Scholar 

  33. C.H. Suresh, A.M. Vargheese, K.P. Vijayalakshmi, N. Mohan, N. Koga, J. Comput. Chem. 29, 1840 (2008)

    Article  CAS  Google Scholar 

  34. M.S. Gordon, M.W. Schmidt, Chapter 41—advances in electronic structure theory: GAMESS a decade later, in Theory and Applications of Computational Chemistry , ed. by C.E. Dykstra, G. Frenking, K. S. Kim, G.E. Scuseria (Elsevier, Amsterdam, 2005), pp. 1167–1189

    Chapter  Google Scholar 

  35. T. Noro, M. Sekiya, T. Koga, Theor Chem Acc 131, 1 (2013)

    Google Scholar 

  36. K.T. Chung, W.R. Thomasson, C.D. Wu-Yuan, J. Appl. Bacteriol. 69, 498 (1990)

    Article  CAS  Google Scholar 

  37. C. Azoro, World J. Bioechnol. 3, 347 (2002)

    Google Scholar 

  38. K. Fukui, T. Yonezawa, H.J. Shingu, J. Chem. Phys. 20, 722 (1952)

    Article  CAS  Google Scholar 

  39. Wahida Boufas, N. Dupont, M. Berredjem, K. Berrezag, I. Becheker, H. Berredjem, N.E. Aouf. J. Mol. Struct. 1074, 180 (2014)

    Article  CAS  Google Scholar 

  40. M. Carcelli, P. Mazza, C. Pelizzi, G. Pelizzi, F. Zani, J. Inorg. Biochem. 57, 43 (1995)

    Article  CAS  Google Scholar 

  41. L. Padmaja, C. Ravikumar, D. Sajan, I.H. Joe, V.S. Jayakumar, G.R. Pettit, O.F. Nielsen, J. Raman Spectrosc. 40, 419 (2009)

    Article  CAS  Google Scholar 

  42. C. Ravikumar, I.H. Joe, V.S. Jayakumar, Chem. Phys. Lett. 460, 552 (2008)

    Article  CAS  Google Scholar 

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Acknowledgements

Guda Mallikarjuna Reddy is grateful to the Brazilian Higher Education Personnel Training Coordination (CAPES: Coordenação de Aperfeiçoamento de Pessoal de Nível Superior) under the PNPD program and authors GMR and GS give thanks to Ural Federal University, Russia.

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Correspondence to Jarem Raul Garcia.

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Reddy, G.M., Sravya, G., Yuvaraja, G. et al. Highly functionalized pyranopyrazoles: synthesis, antimicrobial activity, simulation studies and their structure activity relationships (SARs). Res Chem Intermed 44, 7491–7507 (2018). https://doi.org/10.1007/s11164-018-3569-8

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