Skip to main content
SpringerLink
Log in

Synthesis, characterization and quantum-chemical calculations of novel series of pyridones, quinazolinones and pyrazoles heterocyclic compounds

  • Original Paper
  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

This paper presents a combined synthesis and computational study of novel series of pyridones, quinazolinones and pyrazoles heterocyclic compounds that were characterized by elemental analyses and spectral dada. Michael addition of substituted-2-methoxycarbonylacetanilide 2a, b on the α-substituted cinnamonitriles 3a–d gave the corresponding pyridone and quinazolinone derivatives 5, 6a–c, 7a–d, and 14a–e, respectively. Reaction of ethyl-2-cyano3-ethoxyacrylate with 2a, b afforded the corresponding pyridone 10a, b. Also, spiro pyridine derivative 12 was synthesized through the reaction of 2a, b with indandione malononitrile (11). Reaction of hydrazine and phenyl hydrazine with acrylamido derivatives 15a–d afforded the novel pyrazoles 16 and 17. The molecular modeling of the synthesized compounds has been drawn and their molecular parameters were calculated. Also, valuable information is obtained from the calculation of molecular parameters including electronegativity of the coordination sites, net dipole moment of the compounds, total energy, electronic energy, binding energy, HOMO and LUMO energy.

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

Scheme 1
Scheme 2
Scheme 3
Scheme 4
Scheme 5
Scheme 6
Scheme 7
Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. F.E. Silverstien, G. Faich, J.L. Goldstien, L.S. Simon, T. Pincus, A. Whelton, R. Makuch, G. Eisen, N.M. Agrawal, W.F. Stenson, A.M. Burr, W.W. Zhao, J.D. Kent, J.B. Lefkowith, K.M. Verburg, G.S. Gies, J. Am. Med. Assoc. 284, 1247–1255 (2000)

    Article  Google Scholar 

  2. S. Mark, E. Jan, A. Sabrina, L. Martina, A. Silke, R. Yeon, A. Jodi, S. Gillian, R. William, M. Detlef, E. Stephen, K. Bert, S. Thomas, M. Manfred, Antivir. Res. 79, 49–61 (2008)

    Article  Google Scholar 

  3. H. Kumar, D. Saini, S. Jaina, N. Jain, Eur. J. Med. Chem. 70, 248–258 (2013)

    Article  CAS  Google Scholar 

  4. J. Hanusek, Chem. Listy 95, 811–813 (2001)

    CAS  Google Scholar 

  5. H.J. Chan, J.S. Hong, L.F. Kuyper, D.P. Baccanari, S.S. Joyner, R.L. Tansik, C.M. Boytos, S.K. Rudolph, J. Med. Chem. 38, 3608–3616 (1995)

    Article  CAS  Google Scholar 

  6. R. Castaldo, D. Gump, M.J. Cormack, Antimicrob. Agents Chemother. 15, 81–86 (1979)

    Article  CAS  Google Scholar 

  7. K. Harushia, Y. Kiesuke, H. Seiko, H. Shingo, K. Ryota, H. Norimitsu, M. Makoto, O. Yoshiteru, J. Med. Chem. 49, 4698–4706 (2006)

    Article  Google Scholar 

  8. T. Yasutaka, S. Takao, W. Nobuhisa, A. Hideyuki, S. Shigeru, S. Isao, J. Med. Chem. 37, 2106–2111 (1994)

    Article  Google Scholar 

  9. D. Marianne, P. Fredric, C. Olivier, T. Jean-Claude, C. Jean-Pierre, B. Yves, Chem. Pharm. Bull. 49, 1061–1065 (2001)

    Article  Google Scholar 

  10. Mani Chandrica, P.; Yakaiah, T.; Raghu Ram Rao, A.; Narsaiah, B.; Chakra Reddy, N.; Sridhar, V.; Venkateshwara Rao. J Eur. J. Med. Chem. 43, 846–852 (2008)

    Article  Google Scholar 

  11. M.H. Yen, J.R. Sheu, I.H. Peng, Y. Lee, M. Chern, J. Pharm. Pharmacol. 48, 90–95 (1996)

    Article  CAS  Google Scholar 

  12. S. Hyao, M.J. Mvera, W. Strycker, T. Leipzi, R. Klup, H. Hartzler, J. Med. Chem. 8, 807–811 (1965)

    Article  Google Scholar 

  13. E. Cohen, E. Klarberg, R. JamesVaughan, J. Am. Chem. Soc. 82, 2731–2735 (1960)

    Article  CAS  Google Scholar 

  14. M. Kenji, U. Junko, S. Takashi, I. Michio, A.G. Neil, Y. Jin-Chen, T. Shusuke, O. Shoji, N. Yuji, J. Med. Chem. 46, 4910–4925 (2003)

    Article  Google Scholar 

  15. V.K. Archana, C. Srivastava, K. Ramesh, Indian J. Chem. 41, 2371–2375 (2002)

    Article  Google Scholar 

  16. B. Atsuo, K. Noriaki, M. Haruhiko, O. Yoshikazu, T. Shigehisa, S. Takashi, J. Med. Chem. 39, 5176–5182 (1996)

    Article  Google Scholar 

  17. B.Y. Daniel, W.G. Jason, L.N. Stephanie, V.P. Arely, T.C. Matthew, A.B. David, J. Dermatol. Sci. 42, 13–21 (2006)

    Article  Google Scholar 

  18. J.L. Greene, A.M. Williams, J.A. Montgomery, J. Med. Chem. 7, 20 (1964)

    Article  CAS  Google Scholar 

  19. M.J. Gil, M.A. Manu, C. Arteaga, M. Migliaccio, I. Encio, A. Gonzalez, V. Martinez-Merino, Bioorg. Med. Chem. Lett. 9, 2321 (1999)

    Article  CAS  Google Scholar 

  20. A. Gangjee, Y. Zhu, S.F. Queener, J. Med. Chem. 4, 4533 (1998)

    Article  Google Scholar 

  21. A.P. Krapcho, S.N. Haydar, S. Truong-Chiott, M.P. Hacker, E. Menta, G. Beggiolin, Bioorg. Med. Chem. Lett. 10, 305 (2000)

    Article  CAS  Google Scholar 

  22. F. Monna, F. Chimenti, A. Balasco, B. Bizzarri, W. Filippelli, A. Filippelli, L. Gagliardi, Eur. J. Med. Chem. 34, 245 (1999)

    Article  Google Scholar 

  23. G. Szabo, J. Fischer, A. Kis-Varga, K. Gyires, J. Med. Chem. 51, 142–147 (2008)

    Article  CAS  Google Scholar 

  24. R. Sridhar, P.T. Perumal, S. Etti, G. Shanmugam, M.N. Ponnuswamy, V.R. Prabavathy, N. Mathivanan, Bioorg. Med. Chem. Lett. 14, 6035 (2004)

    Article  CAS  Google Scholar 

  25. M.A.F. Vera-DiVaio, A.C.C. Freitas, H.C.A. Castro, S. de Albuquerque, L.M. Cabral, C.R. Rodrigues, M.G. Albuquerque, R.C.A. Martins, M.G. Henriques, L.R.S. Dias, Bioorg. Med. Chem. 17, 295 (2009)

    Article  CAS  Google Scholar 

  26. A. Tanitame, Y. Oyamada, K. Ofuji, M. Fujimoto, N. Iwai, Y. Hiyama, K. Suzuki, H. Ito, M. Wachi, J. Yamagishi, J. Med. Chem. 47, 3693 (2004)

    Article  CAS  Google Scholar 

  27. M.J. Genin, C. Biles, B.J. Keiser, S.M. Poppe, S.M. Swaney, W.G. Tarpley, Y. Yagi, D.L. Romero, J. Med. Chem. 43, 1034 (2000)

    Article  CAS  Google Scholar 

  28. N. Gokhan-Kelekci, S. Koyunoglu, S. Yabanoglu, K. Yelekci, O. Ozgen, G. Ucar, K. Erol, E. Kendi, A. Yesilada, Bioorg. Med. Chem. 17, 675–689 (2009)

    Article  Google Scholar 

  29. D.M. Shen, E.J. Brady, M.R. Candelore, Q. DallasYang, V.D.H. Ding, W.P. Feeney, G. Jiang, M.E. McCann, S. Mock, S.A. Qureshi, R. Saperstein, X. Shen, X. Tong, L.M. Tota, M.J. Wright, X. Yang, S. Zheng, K.T. Chapman, B.B. Zhang, J.R. Tata, E.R. Parmee, Bioorg. Med. Chem. Lett. 21, 76–81 (2011)

    Article  CAS  Google Scholar 

  30. A. Padmaja, C. Rajasekhar, A. Muralikrishna, V. Padmavathi, Eur. J. Med. Chem. 46, 5034–5038 (2011)

    Article  CAS  Google Scholar 

  31. F. Jensen, Introduction to Computational Chemistry (Wiley, Chichester, 1999)

    Google Scholar 

  32. Y.D. Scherson, S.J. Aboud, J. Wilcox, B.J. Cantwell, J. Phys. Chem. 115, 11036 (2011)

    CAS  Google Scholar 

  33. J.J.P. Stewart, Comp. J. Chem. 10, 209 (1989)

    Article  CAS  Google Scholar 

  34. J.J.P. Stewart, Comp. J. Chem. 16, 221 (1989)

    Article  Google Scholar 

  35. M.H.M. Helal, N.S. Ahmed, M.S. Elwessaly, Y.A. Ammar, Arch. Pharm. Chem. Life Sci. 346, 1–11 (2013)

    Google Scholar 

  36. M.H.M. Helal, M.A. Salem, M.S.A. El-Gaby, M. Aljahdali, Eur. J. Med. Chem. 65, 517–526 (2013)

    Article  CAS  Google Scholar 

  37. M.H.M. Helal, S.Y. Abbas, M.A. Salem, A.A. Farag, Y.A. Ammar, Med. Chem. Res. 22, 5598–5609 (2013)

    Article  CAS  Google Scholar 

  38. M.H. Helal, G.A.M. El-Hag Ali, A.A. Ali, Y.A. Ammar, J. Chem. Res., 465 (2010)

  39. A.A. El-Sherif, M.M. Shoukry, L.O. Abobakr, Spectrochim. Acta (A) 112, 290–300 (2013)

    Article  CAS  Google Scholar 

  40. A.A. El-Sherif, T.M.A. Eldebss, Spectrochim. Acta Part A 79, 1803–1814 (2011)

    Article  CAS  Google Scholar 

  41. M. Aljahdali, A.A. EL-Sherif, Inorg. Chim. Acta 407, 58–68 (2013)

    Article  CAS  Google Scholar 

  42. A.A. El-Sherif, Inorg. Chim. Acta 362, 4991–5000 (2009)

    Article  CAS  Google Scholar 

  43. A.A. El-Sherif, B.J.A. Jeragh, Spectrochim. Acta (A) 68, 877 (2007)

  44. R. Pal, R.N. Handa, H.K. Pujari, J. Indian Chem. Soc. 31B, 771 (1992)

    CAS  Google Scholar 

  45. R.G. Pearson, J. Org. Chem. 54, 1423 (1989)

    Article  CAS  Google Scholar 

  46. R.G. Parr, R.G. Pearson, J. Am. Chem. Soc. 105, 7512 (1983)

    Article  CAS  Google Scholar 

  47. P. Geerlings, F. De Proft, W. Langenaeker, Chem. Rev. 103, 1793 (2003)

    Article  CAS  Google Scholar 

  48. R.G. Parr, J. Am. Chem. Soc. 1999, 121 (1922)

    Google Scholar 

  49. P.K. Chattaraj, S. Giri, J. Phys. Chem. A 111, 11116 (2007)

    Article  CAS  Google Scholar 

  50. G. Speie, J. Csihony, A.M. Whalen, C.G. Pie-Pont, Inorg. Chem. 35, 3519 (1996)

    Article  Google Scholar 

  51. HyperChem version 7.5, Hypercube Inc., Gainesville (2003)

  52. D.H. Brouwer, I.L. Moudrakovski, R.J. Darton, R.E. Morris, Magn. Reson. Chem. 48, S113 (2010)

    Article  CAS  Google Scholar 

  53. K.K. Baldridge, K.I. Hardcastle, T.J. Seiders, J.S. Siegel, Org. Biomol. Chem. 8, 53 (2010)

    Article  CAS  Google Scholar 

  54. V.D. Ghule, P.M. Jadhav, R.S. Patil, S. Radhakrishnan, T. Soman, J. Phys. Chem. A 114, 498 (2010)

    Article  CAS  Google Scholar 

  55. S.W. Xia, X. Xu, Y.L. Sun, Y.L. Fan, Y.H. Fan, C.F. Bi, D.M. Zhang, L.R. Yang, Chin. J. Struct. Chem. 25, 200 (2006)

    Google Scholar 

  56. D.-Q. Zhang, L.-X. Gao, G.-D. Zhou, Corros. Sci. 46, 3031–3040 (2004)

    Article  CAS  Google Scholar 

  57. R.G. Parr, W. Yang (eds.), Density-Functional Theory of Atoms and Molecules (Oxford, New York, 1989)

  58. G. Gao, C. Liang, Electrochim. Acta 52, 4554–4559 (2007)

    Article  CAS  Google Scholar 

  59. Y. Feng, S. Chen, W. Guo, Y. Zhang, G. Liu, J. Electroanal. Chem. 602, 115–122 (2007)

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Al-Azhar University, Nasr City, 11284, Cairo, Egypt

    M. A. Salem, M. H. Helal, T. A. Abd-elaziz & G. A. M. Mohamed

  2. Department of Chemistry, Faculty of Arts and Science, Northern Border University, Rafha, Kingdom of Saudi Arabia

    M. H. Helal & A. A. El-Sherif

  3. Department of Chemistry, Faculty of Science and Arts, King Khalid University, Mohail Assir, Kingdom of Saudi Arabia

    M. A. Salem

  4. Department of Chemistry, Faculty of Science, Cairo University, Giza, Egypt

    Taha M. A. Eldebss & A. A. El-Sherif

Authors
  1. M. A. Salem
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. H. Helal
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Taha M. A. Eldebss
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. T. A. Abd-elaziz
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. A. El-Sherif
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. G. A. M. Mohamed
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Taha M. A. Eldebss.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Salem, M.A., Helal, M.H., Eldebss, T.M.A. et al. Synthesis, characterization and quantum-chemical calculations of novel series of pyridones, quinazolinones and pyrazoles heterocyclic compounds. J IRAN CHEM SOC 12, 1693–1707 (2015). https://doi.org/10.1007/s13738-015-0644-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-015-0644-6

Keywords

Search

Navigation