Skip to main content

Advertisement

SpringerLink
Log in

Quantum chemical, experimental, theoretical spectral (FT-IR and NMR) studies and molecular docking investigation of 4,8,9,10-tetraaryl-1,3-diazaadamantan-6-ones

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

The compounds 4,8,9,10-tetraaryl-1,3-diazaadamantan-6-ones (a–e) were synthesized and characterized by FT-IR, 1H and 13C NMR spectra, and the spectral data have been theoretically analyzed by the DFT method. The electronic properties including a highest occupied molecular orbital (HOMO), lowest unoccupied molecular orbital (LUMO) and related parameters were calculated with B3LYP/6-311 G (d, p) basis set. The observed HOMO and LUMO mappings describe the different charge transfer possibilities within the molecule. Besides, the reactive properties of the molecules have been addressed based on the frontier molecular orbital analysis. The Molecular Electrostatic Potential and Fukui function analysis reveal the sites for electrophilic attack and nucleophilic reactions in the molecule. The intramolecular contacts have been interpreted using Natural Bond Orbital analysis and the thermodynamic properties also presented. The molecular docking study has been executed to study the binding interactions of the synthesized compounds with H1N1 swine virus-M2 proton channel and COX-2 protein.

Graphical abstract

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

Fig. 1
Fig. 2
Scheme 1
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

References

  1. W.L. Davies, R.R. Grunnert, R.F. Haff, J.W. McGahen, E.M. Neumeyer, M. Paulshock, J.C. Watts, T.R. Wood, E.C. Hermann, C.E. Hoffmann, Science 144, 862 (1964)

    Article  CAS  Google Scholar 

  2. Y. Togo, R.B. Hornick, A.T. Dawkins, J. Am. Med. Assoc. 203, 1089 (1968)

    Article  CAS  Google Scholar 

  3. F.G. Hayden, J.M.I. Gwaltney, C.R.L. Van, K.F. Adams, B. Giordani, Antimicrob. Agents Chemother. 19, 226 (1981)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. S. Rabinovich, J.T. Baldini, R. Bannister, Am. J. Med. Sci. 257, 328 (1969)

    Article  CAS  PubMed  Google Scholar 

  5. J. Balzarini, B. Orzeszko, J.K. Maurin, A. Orzeszko, Eur. J. Med. Chem. 42, 993 (2007)

    Article  CAS  PubMed  Google Scholar 

  6. J. Balzarini, B. Orzeszko-Krzesińska, J.K. Maurin, A. Orzeszko, Eur. J. Med. Chem. 44, 303 (2009)

    Article  CAS  PubMed  Google Scholar 

  7. M.A. Al-Omar, E.S. Al-Abdullah, I.A. Shehata, E.E. Habib, T.M. Ibrahim, A.A. El-Emam, Molecules 15, 2526 (2010)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  8. O. Kouatly, A. Geronikaki, C. Kamoutsis, D. Hadjipavlou-Litina, P. Eleftheriou, Eur. J. Med. Chem. 44, 119 (2009)

    Article  CAS  Google Scholar 

  9. A.A. Kadi, E.S. Al-Abdullah, I.A. Shehata, E.E. Habib, T.M. Ibrahim, A.A. El-Emam, Eur. J. Med. Chem. 45, 5006 (2010)

    Article  CAS  PubMed  Google Scholar 

  10. G. Zoidis, I. Papanastasiou, I. Dotsikas, A. Sandoval, R.G. Dos Santos, Z. Papdopoolou-Daifoti, A. Vamvakides, N. Kolocouris, R. Felix, Bioorg. Med. Chem. 13, 2791 (2005)

    Article  CAS  PubMed  Google Scholar 

  11. A. Baxter, J. Bent, K. Bowers, M. Braddock, S. Brough, M. Fagura, M. Lawson, T. McInally, M. Mortimore, M. Robertson, R. Weaver, P. Webborn, Bioorg. Med. Chem. Lett. 13, 4047 (2003)

    Article  CAS  PubMed  Google Scholar 

  12. J.C.E. Owen, P.S. Whitton, Brain Res. 1117, 206 (2006)

    Article  CAS  PubMed  Google Scholar 

  13. E.B. Villhauer, J.A. Brinkman, G.B. Naderi, B.F. Burkey, B.E. Dunning, K. Prasad, B.L. Mangold, M.E. Russell, T.E. Hughes, J. Med. Chem. 46, 2774 (2003)

    Article  CAS  PubMed  Google Scholar 

  14. D.J. Augeri, J.A. Robl, D.A. Betebenner, D.R. Magnin, A. Khanna, J.G. Robertson, A. Wang, L.M. Simpkins, P. Taunk, Q. Huang, S. Han, B. Abboa-Offei, M. Cap, L. Xin, L. Tao, E. Tozzo, G.E. Welzel, D.M. Egan, J. Marcinkeviciene, S.Y. Chang, S.A. Biller, M.S. Kirby, R.A. Parker, L.G. Hamann, J. Med. Chem. 48, 5025 (2005)

    Article  CAS  PubMed  Google Scholar 

  15. M.S. Scherman, E.J. North, V. Jones, T.N. Hess, A.E. Grzegorzewicz, T. Kasagami, I.H. Kim, O. Merzlikin, A.J. Lenaerts, R.E. Lee, M. Jackson, C. Morisseau, M.R. McNeil, Bioorg. Med. Chem. 20, 3255 (2012)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  16. A.A. El-Emam, A.M.S. Al-Tamimi, M.A. Al-Omar, K.A. Alrashood, E.E. Habib, Eur. J. Med. Chem. 68, 96 (2013)

    Article  CAS  PubMed  Google Scholar 

  17. E.J. North, M.S. Scherman, D.F. Bruhn, J.S. Scarborough, M.M. Maddox, V. Jones, A. Grzegorzewicz, L. Yang, T. Hess, C. Morisseau, M. Jackson, M.R. McNeil, R.E. Lee, Bioorg. Med. Chem. 21, 2587 (2013)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  18. E.S. Al-Abdullah, H.M. Al-Tuwaijri, H.M. Hassan, M.A. Al-Alshaikh, E.E. Habib, A.A. El-Emam, Molecules 20, 8125 (2015)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  19. L.H. Al-Wahaibi, H.M. Hassan, A.M. Abo-Kamar, H.A. Ghabbour, A.A. El-Emam, Molecules 22, 710 (2017)

    Article  CAS  PubMed Central  Google Scholar 

  20. G.L. Balaji, S. Sarveswari, V. Vijayakumar, Res. Chem. Intermed. 41, 6765 (2015)

    Article  CAS  Google Scholar 

  21. S. Sivasubramanian, M. Sundaravadivelu, N. Arumugam, Org. Prep. Proced. Int. 22, 645 (1990)

    Article  CAS  Google Scholar 

  22. V. Vijayakumar, M. Sundaravadivelu, S. Perumal, Magn. Reson. Chem. 39, 101 (2001)

    Article  CAS  Google Scholar 

  23. J.F. Wang, D.Q. Wei, K.C. Chou, Biochem. Biophys. Res. Commun. 388, 413 (2009)

    Article  CAS  PubMed  Google Scholar 

  24. K.M. Amin, M.M. Kamel, M.M. Anwar, M. Khedr, Y.M. Syam, Eur. J. Med. Chem. 45, 2117 (2010)

    Article  CAS  PubMed  Google Scholar 

  25. G.M. Morris, D.S. Goodsell, R.S. Halliday, R. Huey, W.E. Hart, R.K. Belew, A.J. Olson, J. Comput. Chem. 19, 1639 (1998)

    Article  CAS  Google Scholar 

  26. M.J. Frisch, J.A. Pople, J.S. Binkley, J. Chem. Phys. 80, 3265 (1984)

    Article  CAS  Google Scholar 

  27. R. Ditchfield, Mol. Phys. 27, 789 (1974)

    Article  CAS  Google Scholar 

  28. C.Y. Panicker, H.T. Varghese, P.S. Nayak, B. Narayana, B.K. Sarojini, H.K. Fun, J.A. War, S.K. Srivastava, C.V. Alsenoy, Spectrochim Acta A 148, 18 (2015)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  30. R.G. Pearson, Proc. Natl. Acad. Sci. USA 83, 8440 (1986)

    Article  CAS  PubMed  Google Scholar 

  31. R.G. Parr, L.V. Szentpaly, S. Liu, J. Am. Chem. Soc. 121, 1922 (1999)

    Article  CAS  Google Scholar 

  32. Z. Zhou, R.G. Parr, J. Am. Chem. Soc. 112, 5720 (1990)

    Article  CAS  Google Scholar 

  33. D. Mahadevan, S. Periandy, M. Karabacak, S. Ramalingam, N. Puviarasan, Spectrochim. Acta A 86, 139 (2012)

    Article  CAS  Google Scholar 

  34. J. Aihara, Theor. Chem. Acc. 102, 134 (1999)

    Article  CAS  Google Scholar 

  35. J. Aihara, J. Phys. Chem. A 103, 7487 (1999)

    Article  CAS  Google Scholar 

  36. T.K. Kuruvilla, J.C. Prasana, S. Muthu, J. George, S. AnnMathew, Spectrochim. Acta A 188, 382 (2018)

    Article  CAS  Google Scholar 

  37. F.A.M. Al-Omary, A. Raj, K. Raju, C. Yohannan Panicker, N.G. Haress, A.A. El-Emam, M.B. El-Ashmawy, A.A. Al-Saadi, C.V. Alsenoy, J. Ahmad War, Spectrochim. Acta A 136, 520 (2015)

    Article  CAS  Google Scholar 

  38. E. Scrocco, J. Tomasi, Adv. Quantum Chem. 11, 115 (1979)

    Article  Google Scholar 

  39. E.J. Luque, J.M. Lopez, M. Orozco, Theor. Chem. Acc. 103, 343 (2000)

    Article  CAS  Google Scholar 

  40. T. Karthick, P. Tandon, J. Mol. Model. 22, 142 (2016)

    Article  CAS  PubMed  Google Scholar 

  41. J. Lu, W.R. Kobertz, C. Deutsch, J. Mol. Biol. 371, 1378 (2007)

    Article  CAS  PubMed  Google Scholar 

  42. N. Uludağ, G. Serdaroğlu, A. Yinanc, J. Mol. Struct. 1161, 152 (2018)

    Article  CAS  Google Scholar 

  43. A. Esme, S.G. Sagdinç, Spectrochim. Acta A 188, 443 (2018)

    Article  CAS  Google Scholar 

  44. F. Weinhold, C.R. Landis, E.D. Glendening, Int. Rev. Phys. Chem. 35, 399 (2016)

    Article  CAS  Google Scholar 

  45. A.E. Reed, L.A. Curtiss, F. Weinhold, Chem. Rev. 88, 899 (1988)

    Article  CAS  Google Scholar 

  46. M. Raja, R. Raj Muhamed, S. Muthu, M. Suresh, J. Mol. Struct. 1141, 284 (2017)

    Article  CAS  Google Scholar 

  47. A.O. Zacharias, A. Varghese, K.B. Akshaya, M.S. Savitha, L. George, J. Mol. Struct. 1158, 1 (2018)

    Article  CAS  Google Scholar 

  48. C. Morell, A. Grand, A. Toro-Labbe, J. Phys. Chem. A 109, 205 (2005)

    Article  CAS  PubMed  Google Scholar 

  49. S. Sevanthi, S. Muthu, M. Raja, J. Mol. Struct. 1173, 251 (2018)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors thank the UGC, New Delhi for Major Research Project (Grant No. 42-358/2013 (SR)) & UGC-Special Assistance Program (SAP). The authors gratefully acknowledge the DST- FIST NMR facility of Department of Chemistry, Gandhigram Rural Institute-Deemed to be University for recording NMR spectra.

Author information

Authors and Affiliations

  1. Department of Chemistry, The Gandhigram Rural Institute-Deemed to be University, Gandhigram, Tamilnadu, 624 302, India

    G. Vengatesh & M. Sundaravadivelu

Authors
  1. G. Vengatesh
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. Sundaravadivelu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to M. Sundaravadivelu.

Ethics declarations

Conflict of interest

The authors declare that they have no conflict of interest in the manuscript.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (PDF 21620 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Vengatesh, G., Sundaravadivelu, M. Quantum chemical, experimental, theoretical spectral (FT-IR and NMR) studies and molecular docking investigation of 4,8,9,10-tetraaryl-1,3-diazaadamantan-6-ones. Res Chem Intermed 45, 4395–4415 (2019). https://doi.org/10.1007/s11164-019-03838-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-019-03838-9

Keywords

Search

Navigation