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Synthesis, Characterization and Bioactivity Studies of S-Allyl-β-N-(1-(4-methoxyphenyl)-ethylidene)dithiocarbazate and its Bis-chelated Cu(II), Ni(II) and Zn(II) Complexes
Corresponding Author(s) : Shrikant B. Jagtap
Asian Journal of Chemistry,
Vol. 34 No. 5 (2022): Vol 34 Issue 5, 2022
Abstract
The general formula M(mAp-sadtc)2 type of metal complexes (where M = Cu2+, Ni2+, Zn2+) were synthesized by reaction of S-allyl-β-N-(1-(4-methoxyphenyl)ethylidene)dithiocarbazate ligand [H-(mAp-sadtc)] with metal(II) acetate salts (M = Ni2+, Cu2+ or Zn2+). The bis-chelated metal complexes were synthesized by subsequent reaction of metal(II) acetate salts and dithiocarbazate ligand in 1:2 proportion, respectively. The metal complexes and dithiocarbazate Schiff base were characterized by available methods like elemental analysis, 1H NMR, UV-Vis spectroscopy, 13C NMR, FT-IR spectroscopy, molar conductance and magnetic moments. Both nitrogen atoms of azomethine moiety (C=N) and deprotonated thiolate sulfur of dithiocarbazate ligand coordinated to the central metal ion formed five-membered rings on chelation. The synthesized dithiocarbazate ligand [H-(mAp-sadtc)] (1) and its bis-chelated M(mAp-sadtc)2 complexes (2-4) were screened for bioactivity against bacterial strains. The antibacterial results show that the metal(II) complexes exhibited significantly prominent antibacterial activity than dithiocarbazate ligand. Among the synthesized bis-chelated metal complexes, Ni-complex exhibited prominent antibacterial and antifungal activity as compared to other metal(II) complexes and ligand.
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References
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A. Núñez-Montenegro, R. Carballo and E.M. Vázquez-López, Polyhedron, 27, 2867 (2008); https://doi.org/10.1016/j.poly.2008.06.018
R.K. Grasselli, Catal. Today, 49, 141 (1999); https://doi.org/10.1016/S0920-5861(98)00418-0
R.J. Cross, P.D. Newman, R.D. Peacock and D. Stirling, J. Mol. Catal. A, 144, 273 (1999); https://doi.org/10.1016/S1381-1169(98)00371-9
M.R. Maurya, S. Dhaka and F. Avecilla, Polyhedron, 81, 154 (2014); https://doi.org/10.1016/j.poly.2014.05.068
K.J. Ivin and J.C. Mol, Olefin Metathesis and Metathesis Polymerization, Academic Press: London (1997).
M.A.A.A.A. Islam, M.C. Sheikh, M.S. Alam, E. Zangrando, M.A. Alam, M.T.H. Tarafder and R. Miyatake, Transition Met. Chem., 39, 141 (2014); https://doi.org/10.1007/s11243-013-9783-8
S. Ponnusamy and N. Ramasamy, Int. J. Mater. Prod. Technol., 55, 142 (2017); http://dx.doi.org/10.1504/IJMPT.2017.084958
M.A. Mumit, M.A.-A.-A.-A. Islam, M.C. Sheikh, R. Miyatake, M.O.A. Mondal and M.A. Alam, J. Mol. Struct., 1178, 583 (2019); https://doi.org/10.1016/j.molstruc.2018.10.046
F.C. Lima, T.S. Silva, C.H.G. Martins and C.C. Gatto, Inorg. Chim. Acta, 483, 464 (2018); https://doi.org/10.1016/j.ica.2018.08.032
N. Nanjundan, R. Narayanasamy, R.J. Butcher, J.P. Jasinski, K. Velmurugan, R. Nandhakumar, M.D. Balakumaran, P.T. Kalaichelvan and V.G. Gnanasoundari, Inorg. Chim. Acta, 455, 283 (2017); https://doi.org/10.1016/j.ica.2016.10.035
N. Nanjundan, P. Selvakumar, R. Narayanasamy, R.A. Haque, K. Velmurugan, R. Nandhakumar, T. Silambarasan and R. Dhandapani, J. Photochem. Photobiol. B, 141, 176 (2014); https://doi.org/10.1016/j.jphotobiol.2014.10.009
C.C. Gatto, M.A.S. Chagas, I.J. Lima, F. Mello Andrade, H.D. Silva, G.R. Abrantes and E.P.S. Lacerda, Transition Met. Chem., 44, 329 (2019); https://doi.org/10.1007/s11243-018-00299-8
M.L. Low, L. Maigre, P. Dorlet, R. Guillot, J.-M. Pagès, K.A. Crouse, C. Policar and N. Delsuc, Bioconjug. Chem., 25, 2269 (2014); https://doi.org/10.1021/bc5004907
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A.H. Mirza, M.A. Ali, P. Bernhardt and I. Asri, Polyhedron, 81, 723 (2014); https://doi.org/10.1016/j.poly.2014.07.033
M. Kudrat-E-Zahan and M.S. Islam, Russ. J. Gen. Chem., 85, 979 (2015); https://doi.org/10.1134/S1070363215040350
E. Zangrando, M.T. Islam, M.A.-A.A.A. Islam, M.C. Sheikh, M.T.H. Tarafder, R. Miyatake, R. Zahan and M.A. Hossain, Inorg. Chim. Acta, 427, 278 (2015); https://doi.org/10.1016/j.ica.2014.12.014
F.C. Lima, Y.A.O. Só, R. Gargano, M. Fujimori, E.L. França, A.C. Honorio-França and C.C. Gatto, J. Mol. Struct., 1212, 128083 (2020); https://doi.org/10.1016/j.molstruc.2020.128083
M. Yazdanbakhsh, R. Takjoo, W. Frank and A. Aghaei Kaju, J. Coord. Chem., 62, 3651 (2009); https://doi.org/10.1080/00958970903144349
D.F.J. Brown and D. Kothari, J. Clin. Path., 28, 779 (1975); https://doi.org/10.1136/jcp.28.10.779
A.W. Bauer, D.M. Perry and W.M.M. Kirby, AMA Arch. Intern. Med., 104, 208 (1959); https://doi.org/10.1001/archinte.1959.00270080034004
M. Yazdanbakhsh, M.M. Heravi, R. Takjoo and W. Frank, Z. Anorg. Allg. Chem., 634, 972 (2008); https://doi.org/10.1002/zaac.200700521
M.S. Begum, E. Zangrando, M.C. Sheikh, R. Miyatake, M.B.H. Howlader, M.N. Rahman and A. Ghosh, Transition Met. Chem., 42, 553 (2017); https://doi.org/10.1007/s11243-017-0160-x
R. Takjoo, S.S. Hayatolgheibi and H. Amiri Rudbari, Inorg. Chim. Acta, 447, 52 (2016); https://doi.org/10.1016/j.ica.2016.03.020
A. Taha, A.A.A. Emara, M.M. Mashaly and O.M.I. Adly, Spectrochim. Acta A Mol. Biomol. Spectrosc., 130, 429 (2014); https://doi.org/10.1016/j.saa.2014.04.007
R. Takjoo and R. Centore, J. Mol. Struct., 1031, 180 (2013); https://doi.org/10.1016/j.molstruc.2012.07.018
E. Zangrando, M.S. Begum, M.C. Sheikh, R. Miyatake, M.M. Hossain, M.M. Alam, M.A. Hasnat, M.A. Halim, S. Ahmed, M.N. Rahman and A. Ghosh, Arab. J. Chem., 10, 172 (2017); https://doi.org/10.1016/j.arabjc.2016.07.019
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T.B.S.A. Ravoof, K.A. Crouse, E.R.T. Tiekink, M.I.M. Tahir, E.N.M. Yusof and R. Rosli, Polyhedron, 133, 383 (2017); https://doi.org/10.1016/j.poly.2017.05.053
W.J. Geary, Chem. Rev., 7, 81 (1971); http://dx.doi.org/10.1016/S0010-8545(00)80009-0