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Vol. 35 No. 8 (2023): Vol 35 Issue 8, 2023

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Synthesis, Characterization, Antioxidant and Antimicrobial Studies of Acenaphthaquinone Based Schiff Base and Its Corresponding Co(II), Ni(II), Cu(II) and Zn(II) Metal Complexes

https://doi.org/10.14233/ajchem.2023.28058
Tushar S. Umasare
Department of Chemistry, Changu Kana Thakur Arts, Commerce and Science College, New Panvel-Raigad, Navi Mumbai-410206, India
https://orcid.org/0000-0002-6794-2030
Sanjay K. Patil
Department of Chemistry, Changu Kana Thakur Arts, Commerce and Science College, New Panvel-Raigad, Navi Mumbai-410206, India
https://orcid.org/0009-0005-1624-2447

Corresponding Author(s) : Tushar S. Umasare

tusharumasare87@gmail.com

Asian Journal of Chemistry, Vol. 35 No. 8 (2023): Vol 35 Issue 8, 2023

Abstract

A new series of transition metal ions viz. Co(II), Ni(II), Cu(II) and Zn(II) complexes in the 1:1, M:L ratio have been synthesized using 1,5-dimethyl-4-((2-oxoacenaphthylen-1(2H)-ylidene)amino)-2-phenyl-1,2-dihydro-3H-pyrazol-3-one, Schiff base as a ligand derived via condensation reaction between acenaphthaquinone and 4-aminoantipyrine in acetonitrile and characterized by elemental analysis, FTIR, UV-VIS, 1H NMR, 13C NMR, LC-MS, powder XRD, atomic absorption measurements and TGA-DSC. Based on magnetic and electronic data, it has been suggested that Co(II), Ni(II) and Cu(II) complexes have octahedral geometry, while zinc(II) complex has tetrahedral geometry. It has also been found that all these complexes except for [ZnLCl2] are paramagnetic. The molar conductance values indicated that Co(II) and Ni(II) complexes are electrolytic and Cu(II) and Zn(II) complexes are non-electrolytic, respectively. The thermal analysis data confirmed the suggested formula, the presence of coordinated and lattice water molecules and the stability of metal(II) complexes. From powder XRD analysis, the average crystallite size of all the compounds was observed within the nanoscale. The DPPH antioxidant studies revealed that the metal(II) complexes showed better antioxidant activities than the ligand. The metal(II) complexes were found to be effective antimicrobial when they were tested in vitro against six bacteria (S. aureus, B. subtilis, Corynebacterium, E. coli, P. vulgaris and S. enterica) and three fungi (A. oryzae, A. niger and C. albicans).

Keywords

Schiff base Metal(II) complexes Acenaphthaquinone Antioxidant activity Biological activities
Umasare, T. S., & Patil, S. K. (2023). Synthesis, Characterization, Antioxidant and Antimicrobial Studies of Acenaphthaquinone Based Schiff Base and Its Corresponding Co(II), Ni(II), Cu(II) and Zn(II) Metal Complexes. Asian Journal of Chemistry, 35(8), 1932–1942. https://doi.org/10.14233/ajchem.2023.28058
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References
  1. J. Ceramella, D. Iacopetta, A. Catalano, F. Cirillo, R. Lappano and M.S. Sinicropi, Antibiotics, 11, 191 (2022); https://doi.org/10.3390/antibiotics11020191
  2. G. Ceyhan, C. Çelik, S. Urus, I. Demirtas, M. Elmastas and M. Tümer, Spectrochim. Acta A Mol. Biomol. Spectrosc., 81, 184 (2011); https://doi.org/10.1016/j.saa.2011.05.106
  3. S.V. Bhandari, K.G. Bothara, M.K. Raut, A.A. Patil, A.P. Sarkate and V.J. Mokale, Bioorg. Med. Chem., 16, 1822 (2008); https://doi.org/10.1016/j.bmc.2007.11.014
  4. Y.-Z. Xiong, F.-E. Chen, J. Balzarini, E. De Clercq and C. Pannecouque, Eur. J. Med. Chem., 43, 1230 (2008); https://doi.org/10.1016/j.ejmech.2007.08.001
  5. D. Sriram, P. Yogeeswari, N.S. Myneedu and V. Saraswat, Bioorg. Med. Chem. Lett., 16, 2127 (2006); https://doi.org/10.1016/j.bmcl.2006.01.050
  6. K. Sridhar, S.N. Pandeya, J.P. Stables and A. Ramesh, Eur. J. Pharm. Sci., 16, 129 (2002); https://doi.org/10.1016/S0928-0987(02)00077-5
  7. J.P. Kaplan, B.M. Raizon, M. Desarmenien, P. Feltz, P.M. Headley, P. Worms, K.G. Lloyd and G. Bartholini, J. Med. Chem., 23, 702 (1980); https://doi.org/10.1021/jm00180a029
  8. A. Das, M.D. Trousdale, S. Ren and E.J. Lien, Antiviral Res., 44, 201 (1999); https://doi.org/10.1016/S0166-3542(99)00070-4
  9. J. Patole, D. Shingnapurkar, S. Padhye and C. Ratledge, Bioorg. Med. Chem. Lett., 16, 1514 (2006); https://doi.org/10.1016/j.bmcl.2005.12.035
  10. G. Hu, G. Wang, N. Duan, X. Wen, T. Cao, S. Xie and W. Huang, Acta Pharm. Sin. B, 2, 312 (2012); https://doi.org/10.1016/j.apsb.2011.11.003
  11. M. Bheemarasetti, K. Palakuri, S. Raj, P. Saudagar, D. Gandamalla, N.R. Yellu and L.R. Kotha, J. Iran Chem. Soc., 15, 1377 (2018); https://doi.org/10.1007/s13738-018-1338-7
  12. R. Mladenova, M. Ignatova, N. Manolova, T. Petrova and I. Rashkov, Eur. Polym. J., 38, 989 (2002); https://doi.org/10.1016/S0014-3057(01)00260-9
  13. Y. Liu and Z. Yang, J. Organomet. Chem., 694, 3091 (2009); https://doi.org/10.1016/j.jorganchem.2009.05.031
  14. S.C. Sharma, Bull. Chem. Soc. Jpn., 40, 2422 (1967); https://doi.org/10.1246/bcsj.40.2422
  15. D. Modi, S.S. Sabnis and C.V. Deliwala, J. Med. Chem., 13, 935 (1970); https://doi.org/10.1021/jm00299a031
  16. D.K. Johnson, T.B. Murphy, T.B. Rose, W.H. Goodwin and L. Pickart, Inorg. Chim. Acta, 67, 159 (1982); https://doi.org/10.1016/S0020-1693(00)85058-6
  17. E.S.H. ElAshry, H.A. Hamid, A.A. Kassem and M. Shoukry, Molecules, 7, 155 (2002); https://doi.org/10.3390/70200155
  18. Z. Zhang, H. Yang, G. Wu, Z. Li, T. Song and X.Q. Li, Eur. J. Med. Chem., 46, 3909 (2011); https://doi.org/10.1016/j.ejmech.2011.05.062
  19. Y.S. El-Alawi, B.J. McConkey, D. George Dixon and B.M. Greenberg, Ecotoxicol. Environ. Saf., 51, 12 (2002); https://doi.org/10.1006/eesa.2001.2108
  20. C.R. William and J.S. William, Chem. Abstr, 116, 214369 (1992).
  21. A.E.G. Pearson and A.K. Powell, Br. J. Cancer, 9, 204 (1955); https://doi.org/10.1038/bjc.1955.15
  22. C.K. Cain, Chem. Abstr., 72, 12767 (1970).
  23. S. Kumar, A. Hansda, A. Chandra, A. Kumar, M. Sithambaresan, M. Kumar, M.S.H. Faizi, V. Kumar and R.P. John, Polyhedron, 134, 11 (2017); https://doi.org/10.1016/j.poly.2017.05.055
  24. U. El-Ayaan and A.A. Abdel-Aziz, Eur. J. Med. Chem., 40, 1214 (2005); https://doi.org/10.1016/j.ejmech.2005.06.009
  25. M. Rodriguez-Arguelles, M. Ferrari, G. Fava, C. Pelizzi, G. Pelosi, R. Albertini, A. Bonati, P.P. Dall’Aglio, P. Lunghi and S. Pinelli, J. Inorg. Biochem., 66, 7 (1997); https://doi.org/10.1016/S0162-0134(96)00146-8
  26. M. Girges, M. Abou El-Zahab and M.A. Hanna, Arch. Pharm. Res., 11, 169 (1988); https://doi.org/10.1007/BF02861305
  27. A.E. Rubtsov, R.R. Makhmudov, N.V. Kovylyaeva, N.I. Prosyanik, A.V. Bobrov and V.V. Zalesov, Pharm. Chem. J., 36, 608 (2002); https://doi.org/10.1023/A:1022669432631
  28. T. Ito, C. Goto and K. Noguchi, Anal. Chim. Acta, 443, 41 (2001); https://doi.org/10.1016/S0003-2670(01)01192-8
  29. E. Radzikowska, K. Onish and E. Chojak, Eur. J. Cancer, 31, S225 (1995); https://doi.org/10.1016/0959-8049(95)96324-7
  30. M.M.F. Ismail, Y.A. Ammar, H.S.A. El-Zahaby, S.I. Eisa and S. El-Sayed Barakat, Arch. Pharm., 340, 476 (2007); https://doi.org/10.1002/ardp.200600197
  31. M. Mahmoud, R. Abdel-Kader, M. Hassanein, S. Saleh and S. Botros, Eur. J. Pharmacol., 569, 222 (2007); https://doi.org/10.1016/j.ejphar.2007.04.061
  32. S.M. Sondhi, V.K. Sharma, R.P. Verma, N. Singhal, R. Shukla, R. Raghubir and M.P. Dubey, Synthesis, 878 (1999); https://doi.org/10.1055/s-1999-3472
  33. S.M. Sondhi, N. Singhal, R.P. Verma and S.K. Arora, Indian J. Chem., 40B, 113 (2001).
  34. S. Bondock, R. Rabie, H.A. Etman and A.A. Fadda, Eur. J. Med. Chem., 43, 2122 (2008); https://doi.org/10.1016/j.ejmech.2007.12.009
  35. S. Cunha, S.M. Oliveira, M.T. Rodrigues Jr., R.M. Bastos, J. Ferrari, C.M.A. de Oliveira, L. Kato, H.B. Napolitano, I. Vencato and C. Lariucci, J. Mol. Struct., 752, 32 (2005); https://doi.org/10.1016/j.molstruc.2005.05.016
  36. A.P. Mishra, J. Indian Chem. Soc., 76, 35 (1999).
  37. N. Raman, A. Kulandaisamy and K. Jeyasubramanian, Synth. React. Inorg. Met.-Org. Nano-Met. Chem., 32, 1583 (2002); https://doi.org/10.1081/SIM-120015081
  38. K.S. Abou Melha, G.A. Al-Hazmi, I. Althagafi, A. Alharbi, A.A. Keshk, F. Shaaban and N. El-Metwaly, Bioinorg. Chem. Appl., 2021, 6674394 (2021); https://doi.org/10.1155/2021/6674394
  39. I.P. Ejidike and P.A. Ajibade, Molecules, 20, 9788 (2015); https://doi.org/10.3390/molecules20069788
  40. M. Yadav, S. Sharma and J. Devi, J. Chem. Sci., 133, 21 (2021); https://doi.org/10.1007/s12039-020-01854-6
  41. M. Balouiri, M. Sadiki and S.K. Ibnsouda, J. Pharm. Anal., 6, 71 (2016); https://doi.org/10.1016/j.jpha.2015.11.005
  42. A.N. Al-Shareefi, S.H. Kadhim and W.A. Jawad, J. Appl. Chem., 2, 438 (2013).
  43. A.J. Abdulghani and Z.Z. Ahmed, Pak. J. Chem., 1, 100 (2011); https://doi.org/10.15228/2011.v01.i03.p01
  44. M. Manjunath, A. Kulkarni, G. Bagihalli, S. Malladi and S. Patil, J. Mol. Struct., 1127, 314 (2017); https://doi.org/10.1016/j.molstruc.2016.07.123
  45. R.B. Bennie, S.T. David, C. Joel and S.D. Abraham, Int. J. Inorg. Bioinorg. Chem., 5, 49 (2015).
  46. I. Mhaidat, Z.A. Taha, W. Al Momani and A.K. Hijazi, Russ. J. Gen. Chem., 89, 2584 (2019); https://doi.org/10.1134/S1070363219120399
  47. R.S. Bhaskar, C.A. Ladole, N.G. Salunkhe, J.M. Barabde and A.S. Aswar, Arab. J. Chem., 13, 6559 (2020); https://doi.org/10.1016/j.arabjc.2020.06.012
  48. R. Bhaskar, N. Salunkhe, A. Yaul and A. Aswar, Spectrochim. Acta A Mol. Biomol. Spectrosc., 151, 621 (2015); https://doi.org/10.1016/j.saa.2015.06.121
  49. A. Reiss, N. Cioatera, A. Dobritescu, M. Rotaru, A.C. Carabet, F. Parisi, A. Ganescu, I. Dabuleanu, C.I. Spînu and P. Rotaru, Molecules, 26, 3062 (2021); https://doi.org/10.3390/molecules26103062
  50. R.G. Chaudhary, H.D. Juneja, R. Pagadala, N.V. Gandhare and M.P. Gharpure, J. Saudi Chem. Soc., 19, 442 (2015); https://doi.org/10.1016/j.jscs.2014.06.002
  51. F.A. Al-Saif, Int. J. Electrochem. Sci., 8, 10424 (2013); https://doi.org/10.1016/S1452-3981(23)13119-1
  52. K.S. Rahman, F. Haque, N.A. Khan, M.A. Islam, M.M. Alam, Z.A. Alothman, K. Sopian and N. Amin, Chalcogenide Lett., 11, 129 (2014).
  53. P. Chelvanathan, Y. Yusoff, F. Haque, M. Akhtaruzzaman, M.M. Alam, Z.A. Alothman, M.J. Rashid, K. Sopian and N. Amin, Appl. Surf. Sci., 334, 138 (2015); https://doi.org/10.1016/j.apsusc.2014.08.155
  54. M.A. Mahmud, N.K. Elumalai, M.B. Upama, D. Wang, F. Haque, M. Wright, C. Xu and A. Uddin, Sol. Energy Mater. Sol. Cells, 167, 70 (2017); https://doi.org/10.1016/j.solmat.2017.03.032
  55. S. Tetteh, D.K. Dodoo, R. Appiah-Opong and I.J. Tuffour, Inorg. Chem., 2014, 1 (2014); https://doi.org/10.1155/2014/586131
  56. N.P. Priya, S.V. Arunachalam, N. Sathya, V. Chinnusamy and C. Jayabalakrishnan, Transition Met. Chem., 34, 437 (2009); https://doi.org/10.1007/s11243-009-9214-z
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