Issue

Vol. 37 No. 9 (2025): Vol 37 Issue 9, 2025

Copyright (c) 2025 Lonibala Rajkumari, S. Saya Devi , Rodi Laishram, Amar Ningthoujam, Somananda Meetei Soubam, Sureshkumar Singh S.

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis, Spectral Characterization, Density Functional Theory Studies and Antidiabetic Activities of Copper(II) Complexes of Schiff Bases Derived from N-Benzoyl Glycylhydrazide

https://doi.org/10.14233/ajchem.2025.33944
Sapam Saya Devi
Department of Chemistry, Manipur University, Canchipur-795003, India
https://orcid.org/0009-0002-9084-3847
Rodi Laishram
Department of Chemistry, Manipur University, Canchipur-795003, India
https://orcid.org/0009-0006-0092-6358
Amar Ningthoujam
Department of Chemistry, Manipur University, Canchipur-795003, India
https://orcid.org/0000-0002-1213-4722
Soubam Somananda Meetei
Department of Chemistry, Manipur University, Canchipur-795003, India
https://orcid.org/0009-0002-7934-9741
S. Sureshkumar Singh
Department of Botany, Manipur University, Canchipur-795003, India
https://orcid.org/0000-0002-8491-7187
Rajkumari Lonibala
Department of Chemistry, Manipur University, Canchipur-795003, India

Corresponding Author(s) : Rajkumari Lonibala

lonibala@manipuruniv.ac.in

Asian Journal of Chemistry, Vol. 37 No. 9 (2025): Vol 37 Issue 9, 2025

Abstract

Two new Schiff bases, (E)-N-(2-(2-(2-hydroxy-3-methoxybenzylidene)hydrazineyl)-2-oxyethyl)benzylidene)hydrazineyl)-2-oxyethyl)-benzamide (H2L1), (E)-N-(2-((2-hydroxynapthalen-1-yl)methylene)hydrazineyl)-2-oxyethyl)benzamide (H2L2) and their Cu(II) complexes were synthesized and characterized by elemental analyses, molar conductance, thermal analysis, magnetic susceptibility, UV-Vis, IR, EPR and mass spectroscopic data. Formation of Cu(II) complexes having 1:1 metal: ligand stoichiometry was ascertained from the elemental and thermogravemetric analyses. The observed magnetic moment is consistent with the expected value for Cu(II) (d9) complexes, which typically exhibit one unpaired electron. Spectral and DFT studies suggest pentacoordinated geometries for the complexes in which the ligands act as a tridentate species bonding through the carbonyl-O, azomethine-N and phenolate/phenolic-O. The molecular geometries of the complexes were thoroughly optimized using the Global Hybrid Minnesota functional M06, with the Pople 6-31+G(d,p) basis set for oxygen and nitrogen and the Def2-SVP basis set for hydrogen, carbon and heavy transition metal copper atom in the DFT calculations to improve the balance between accuracy and computational cost. The antidiabetic properties of the ligands and their Cu(II) complexes were investigated, revealing that the complexes exhibited significant enzyme inhibition activity.

Keywords

Schiff bases Copper ion Pentacoordinated Tridentate DFT studies Antidiabetic activities
(1)
Devi, S. S.; Laishram, R.; Ningthoujam, A.; Meetei, S. S.; Singh, S. S.; Lonibala, R. Synthesis, Spectral Characterization, Density Functional Theory Studies and Antidiabetic Activities of Copper(II) Complexes of Schiff Bases Derived from N-Benzoyl Glycylhydrazide. ajc 2025, 37, 2123-2134.
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. E. Raczuk, B. Dmochowska, J. Samaszko-Fiertek and J. Madaj, Molecules, 27, 787 (2022); https://doi.org/10.3390/molecules27030787
  2. A.I.A. Soliman, M. Sayed, M.M. Elshanawany, O. Younis, M. Ahmed, A.M. Kamal El-Dean, A.-M.A. Abdel-Wahab, J. Wachtveitl, M. Braun, P. Fatehi and M.S. Tolba, ACS Omega, 7, 10178 (2022); https://doi.org/10.1021/acsomega.1c06636
  3. M. Arifuzzaman, M.R. Karim, T.A. Siddiquee, A.H. Mirza and M.A. Ali, Int. J. Org. Chem., 03, 81 (2013); https://doi.org/10.4236/ijoc.2013.31009
  4. E. Sinn and C.M. Harris, Coord. Chem. Rev., 4, 391 (1969); https://doi.org/10.1016/S0010-8545(00)80080-6
  5. P.B. Sreeja, M.R. Prathapachandra Kurup, A. Kishore and C. Jasmin, Polyhedron, 23, 575 (2004); https://doi.org/10.1016/j.poly.2003.11.005
  6. P.B. Sreeja and M.R.P. Kurup, Spectrochim. Acta A Mol. Biomol. Spectrosc., 61, 331 (2005); https://doi.org/10.1016/j.saa.2004.04.001
  7. D. Kovala-Demertzi, A. Domopoulou, M.A. Demertzis, G. Valle and A. Papageorgiou, J. Inorg. Biochem., 68, 147 (1997); https://doi.org/10.1016/S0162-0134(97)00087-1
  8. D. Kovala-Demertzi, M.A. Demertzis, V. Varagi, A. Papageorgiou, D. Mourelatos, E. Mioglou, Z. Iakovidou and A. Kotsis, Chemotherapy, 44, 421 (1998); https://doi.org/10.1159/000007154
  9. M. Tümer, H. Köksal, M.K. Sener and S. Serin, Transition Met. Chem., 24, 414 (1999); https://doi.org/10.1023/A:1006973823926
  10. N. Raman, J. Dhaveethu Raja and A. Sakthivel, J. Chem. Sci., 119, 303 (2007); https://doi.org/10.1007/s12039-007-0041-5
  11. E.W. Ainscough, A.M. Brodie, A.J. Dobbs, J.D. Ranford and J.M. Waters, Inorg. Chim. Acta, 267, 27 (1998); https://doi.org/10.1016/S0020-1693(97)05548-5
  12. B. Koçyigit Kaymakçioglu and S. Rollas, Farmaco, 57, 595 (2002); https://doi.org/10.1016/S0014-827X(02)01255-7
  13. S.N. Pandeya, D. Sriram, G. Nath and E. De Clercq, Farmaco, 54, 624 (1999); https://doi.org/10.1016/S0014-827X(99)00075-0
  14. E.M. Hodnett and W.J. Dunn, J. Med. Chem., 13, 768 (1970); https://doi.org/10.1021/jm00298a054
  15. J. Vanèo, J. Marek, Z. Trávníèek, E. Raèanská, J. Muselík and O. Švajlenová, J. Inorg. Biochem., 102, 595 (2008); https://doi.org/10.1016/j.jinorgbio.2007.10.003
  16. A. Hameed, M. Al-Rashida, M. Uroos, S. Abid Ali and K.M. Khan, Expert Opin. Ther. Pat., 27, 63 (2017); https://doi.org/10.1080/13543776.2017.1252752
  17. C.M. Sharaby, Spectrochim. Acta A Mol. Biomol. Spectrosc., 66, 1271 (2007); https://doi.org/10.1016/j.saa.2006.05.030
  18. M. Hosseini, Z. Vaezi, M.R. Ganjali, F. Faridbod, S.D. Abkenar, K. Alizadeh and M. Salavati-Niasari, Spectrochim. Acta A Mol. Biomol. Spectrosc., 75, 978 (2010); https://doi.org/10.1016/j.saa.2009.12.016
  19. X. Zhong, Z. Li, R. Shi, L. Yan, Y. Zhu and H. Li, ACS Appl. Nano Mater., 5, 13998 (2022); https://doi.org/10.1021/acsanm.2c03477
  20. J. Costamagna, J. Vargas, R. Latorre, A. Alvarado and G. Mena, Coord. Chem. Rev., 119, 67 (1992); https://doi.org/10.1016/0010-8545(92)80030-U
  21. P.G. Cozzi, Chem. Soc. Rev., 33, 410 (2004); https://doi.org/10.1039/B307853C
  22. L.H. Uppadine, J.-P. Gisselbrecht and J.-M. Lehn, Chem. Commun., 718–719, 718 (2004); https://doi.org/10.1039/B315352E
  23. A. Wood, W. Aris and D.J.R. Brook, Inorg. Chem., 43, 8355 (2004); https://doi.org/10.1021/ic0492688
  24. M.R. Bermejo, R. Pedrido, A.M. González-Noya, M.J. Romero, M. Vázquez and L. Sorace, New J. Chem., 27, 1753 (2003); https://doi.org/10.1039/B305354G
  25. S. Naskar, M. Corbella, A.J. Blake and S.K. Chattopadhyay, Dalton Trans., 1150 (2007); https://doi.org/10.1039/b615004g
  26. R. Ganguly, B. Sreenivasulu and J.J. Vittal, Coord. Chem. Rev., 252, 1027 (2008); https://doi.org/10.1016/j.ccr.2008.01.005
  27. M.J. O’Donnell, Tetrahedron, 75, 3667 (2019); https://doi.org/10.1016/j.tet.2019.03.029
  28. A. Anagnostopoulos and S. Hadjispyrou, J. Inorg. Biochem., 57, 279 (1995); https://doi.org/10.1016/0162-0134(94)00033-7
  29. P.D. Thangjam and L. Rajkumari, J. Chem. Eng. Data, 55, 1166 (2010); https://doi.org/10.1021/je900583g
  30. T. Devi and R. Lonibala, Asian J. Chem., 22, 5369 (2010).
  31. T. Devi and R. Lonibala, Orient. J. Chem., 30, 2029 (2014); https://doi.org/10.13005/ojc/300468
  32. R.K. Lonibala, T.R. Rao and R.K.B. Devi, J. Chem. Sci., 118, 327 (2006); https://doi.org/10.1007/BF02708526
  33. A. Bhunia, S. Manna, S. Mistri, A. Paul, R.K. Manne, M.K. Santra, V. Bertolasi and S. Chandra Manna, RSC Adv., 5, 67727 (2015); https://doi.org/10.1039/C5RA12324K
  34. K. Nejati, A. Bakhtiari, R. Bikas and J. Rahimpour, J. Mol. Struct., 1192, 217 (2019); https://doi.org/10.1016/j.molstruc.2019.04.135
  35. A.V. Marenich, S.V. Jerome, C.J. Cramer and D.G. Truhlar, J. Chem. Theory Comput., 8, 527 (2012); https://doi.org/10.1021/ct200866d
  36. A.I. Vogel, A Text Book of Quantitative Inorganic Analysis, London: ELBS & Longsman, pp. 358-460 (1961).
  37. D. Kumar, H. Kumar, J.R. Vedasiromoni and B.C. Pal, Phytochem. Anal., 23, 421 (2012); https://doi.org/10.1002/pca.1375
  38. B.G. Janesko, K.B. Wiberg, G. Scalmani and M.J. Frisch, J. Chem. Theory Comput., 12, 3185 (2016); https://doi.org/10.1021/acs.jctc.6b00343
  39. Y. Zhao and D.G. Truhlar, Theor. Chem. Acc., 120, 215 (2008); https://doi.org/10.1007/s00214-007-0310-x
  40. R. Ditchfield, W.J. Hehre and J.A. Pople, J. Chem. Phys., 54, 724 (1971); https://doi.org/10.1063/1.1674902
  41. F. Weigend, Phys. Chem. Chem. Phys., 8, 1057 (2006); https://doi.org/10.1039/b515623h
  42. F. Weigend and R. Ahlrichs, Phys. Chem. Chem. Phys., 7, 3297 (2005); https://doi.org/10.1039/b508541a
  43. T.R. Rao, M. Sahay and R.C. Aggarwal, Synth. React. Inorg. Met.-Org. Chem., 15, 209 (1985); https://doi.org/10.1080/00945718508059381
  44. W.J. Geary, Coord. Chem. Rev., 7, 81 (1971); https://doi.org/10.1016/S0010-8545(00)80009-0
  45. M.L. Dianu, A. Kriza and A.M. Musuc, J. Therm. Anal. Calorim., 112, 585 (2013); https://doi.org/10.1007/s10973-012-2578-x
  46. G. Bannach, A.B. Siqueira, E.Y. Ionashiro, E.C. Rodrigues and M. Ionashiro, J. Therm. Anal. Calorim., 90, 873 (2007); https://doi.org/10.1007/s10973-005-7060-6
  47. W. Ferenc and A. Walków-Dziewulska, J. Therm. Anal. Calorim., 63, 865 (2001); https://doi.org/10.1023/A:1010120911658
  48. L.V. Ababei, A. Kriza, A.M. Musuc, C. Andronescu and E.A. Rogozea, J. Therm. Anal. Calorim., 101, 987 (2010); https://doi.org/10.1007/s10973-009-0560-z
  49. K. Nakamoto, Infrared and Raman Spectra of Inorganic and Coordi-nation Compounds, Wiley: New York, edn. 4 (1986).
  50. A. Braibanti, F. Dallavalle, M.A. Pellinghelli and E. Leporati, Inorg. Chem., 7, 1430 (1968); https://doi.org/10.1021/ic50065a034
  51. A.B.P. Lever and H.B. Gray, Acc. Chem. Res., 11, 348 (1978); https://doi.org/10.1021/ar50129a005
  52. K.B. Gudasi, S.A. Patil, R.S. Vadavi, R.V. Shenoy and M.S. Patil, J. Serb. Chem. Soc., 71, 529 (2006); https://doi.org/10.2298/JSC0605529G
  53. D.E. Billing and B.J. Hathaway, J. Chem. Phys., 50, 1476 (1969); https://doi.org/10.1063/1.1671216
  54. B.J. Hathaway and P.G. Hodgson, J. Inorg. Nucl. Chem., 35, 4071 (1973); https://doi.org/10.1016/0022-1902(73)80395-1
  55. R.C. Van Landschoot, J.A.M. Van Hest and J. Reedijk, J. Inorg. Nucl. Chem., 38, 185 (1976); https://doi.org/10.1016/0022-1902(76)80081-4
  56. B.A. Goodman and J.B. Raynor, Adv. Inorg. Chem., 13, 135 (1970); https://doi.org/10.1016/S0065-2792(08)60336-2
  57. D.X. West, J. Inorg. Nucl. Chem., 43, 3169 (1981); https://doi.org/10.1016/0022-1902(81)80082-6
  58. A. Bencini, I. Bertini, D. Gatteschi and A. Scozzafava, Inorg. Chem., 17, 3194 (1978); https://doi.org/10.1021/ic50189a047
  59. J.A. Howard, R. Sutcliffe, J.S. Tse and B. Mile, Chem. Phys. Lett., 94, 561 (1983); https://doi.org/10.1016/0009-2614(83)85056-8
  60. L.V. Azaroff and M.J. Bueger, The Powder Method in X-Ray Crystallography, New York: McGraw Hill (1958).
  61. P. Debnath, P. Debnath, Th.S. Devi, S.S.K. Singh, A. Bhattacharya, K.S. Singh, M. Roy and T.K. Misra, J. Coord. Chem., 75, 3015 (2022); https://doi.org/10.1080/00958972.2022.2155145
  62. P. Debnath, K.S. Singh, K.K. Singh, S. Sureshkumar Singh, L. Sieroñ and W. Maniukiewicz, New J. Chem., 44, 5862 (2020); https://doi.org/10.1039/D0NJ00536C
  63. M. Roy, S. Roy, K.S. Singh, J. Kalita and S.S. Singh, New J. Chem., 40, 1471 (2016); https://doi.org/10.1039/C5NJ02637G
  64. M. Roy, S. Roy, K.S. Singh, J. Kalita and S.S. Singh, Inorg. Chim. Acta, 439, 164 (2016); https://doi.org/10.1016/j.ica.2015.10.012
  65. N.H. Nasaruddin, S.N. Ahmad, S.S. Sirat, T.K. Wai, N.A. Zakaria and H. Bahron, J. Mol. Struct., 1232, 130066 (2021); https://doi.org/10.1016/j.molstruc.2021.130066
  66. A.J. Stasyuk, M. Solà and A.A. Voityuk, Sci. Rep., 8, 2882 (2018); https://doi.org/10.1038/s41598-018-21240-0
Read More
Author biographies is not available.
Crossref
Scopus
Google Scholar
Europe PMC
Download
PDF
Statistic
Read Counter : 220 Download : 212
PlumX