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Novel Gold(III), Palladium(II) and Copper(II) Schiff Base Complexes Derived from 1-Hydroxy-2-acetonaphthone and Phenylethyl Amine: Synthesis, Characterization and Biological Studies
Corresponding Author(s) : V.S. Ingle
Asian Journal of Chemistry,
Vol. 35 No. 2 (2023): Vol 35 Issue 2, 2023
Abstract
In this work, a novel Schiff base from 1-hydroxy-2-acetonaphthone and phenyl ethylamine and its metal complexes were synthesized and characterized using UV-visible, FT-IR, 1H and 13C NMR, SC-XRD, LCMS, TGA-DSC and powder X-ray diffraction. The IR data indicated that the ligand was coordinated via bidentate bonding through the oxygen atom of naphthone and nitrogen atom of azomethine unit. The TGA-DSC analysis of Au(III), Pd(II), and Cu(II) revealed the presence of coordinated water molecules. According to powder X-ray diffraction data, the Schiff base ligand exhibits a tetragonal crystal structure, Au(III) complex has a cubic crystal structure, while Pd(II) and Cu(II) complexes have monoclinic crystal structures. The synthesized metal complexes were examined for their in vitro antibacterial bioactivity against the Gram-negative bacteria E. coli, P. aeruginosa and Gram-positive S. aureus, B. subtilis as well as their in vitro antifungal activity against the two fungus C. albicans and A. niger. According to the biological findings, the synthesized metal complexes exhibited better antimicrobial activities compared to the Schiff base ligand. Similar, outcomes were followed in the antioxidant activity analysis, where the synthesized Schiff base metal complexes had DPPH radical scavenging activity.
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- A. Atahan and S. Durmus, Spectrochim. Acta A Mol. Biomol., 144, 61 (2015); https://doi.org/10.1016/j.saa.2015.01.085
- S. Bag, P.K. Bhaumik, S. Jana, M. Das, P. Bhowmik and S. Chattopadhyay, Polyhedron, 65, 229 (2013); https://doi.org/10.1016/j.poly.2013.08.028
- B.T. Vhanale, N.J. Deshmukh and A.T. Shinde, Heliyon, 5, e02774 (2019); https://doi.org/10.1016/j.heliyon.2019.e02774
- F.T. Esmadi, O.F. Khabour, K. Abbas, A.E. Mohammad, R.T. Obeidat and D. Mfady, Drug Chem Toxicol., 39, 41 (2016); https://doi.org/10.3109/01480545.2015.1017882
- S. Kumar, D.N. Dhar and P.N. Saxena, J. Sci. Ind. Res., 68, 181 (2009); http://nopr.niscpr.res.in/handle/123456789/3170
- Y.M. Ahmed, M.M. Omar and G.G. Mohamed, J. Iran. Chem. Soc., 19, 901 (2022); https://doi.org/10.1007/s13738-021-02359-w
- M. Pal, D. Musib and M. Roy, New J. Chem., 45, 1924 (2021); https://doi.org/10.1039/D0NJ04578K
- S. Makar, T. Saha and S.K. Singh, Eur. J. Med. Chem., 161, 252 (2019); https://doi.org/10.1016/j.ejmech.2018.10.018
- M.A. Abozeid, A.A. El-Sawi, M. Abdelmoteleb, H. Awad, M.M. Abdel-Aziz, A.-R.H. Abdel-Rahmana and E.-S.I. El-Desoky, RSC Adv., 10, 42998 (2020); https://doi.org/10.1039/D0RA08526J
- P. Pandey, A. Verma, K. Bretosh, J. Sutter and S.S. Sunkari, Polyhedron, 164, 80 (2019); https://doi.org/10.1016/j.poly.2019.02.037
- A.S. Al-Bogami, A.M. Al-Majid, M.A. Al-Saad, A.A. Mousa, S.A. Al-Mazroa and H.Z. Alkhathlan, Molecules, 14, 2147 (2009); https://doi.org/10.3390/molecules14062147
- C. Balakrishna, V. Kandula, R. Gudipati, S. Yennam, P.U. Devi and M. Behera, Synlett, 29, 1087 (2018); https://doi.org/10.1055/s-0036-1591898
- D. Banik, J. Kuchlyan, A. Roy, N. Kundu and N. Sarkar, J. Phys. Chem. B, 119, 2310 (2015); https://doi.org/10.1021/jp5064879
- S. Roy, A. Maity, N. Mudi, M. Shyamal and A. Misra, Photochem. Photobiol. Sci., 18, 1342 (2019); https://doi.org/10.1039/c8pp00558c
- N. Sarkar, P.K. Bhaumik, S. Chattopadhyay, Polyhedron, 115, 37 (2016); https://doi.org/10.1016/j.poly.2016.04.013
- B.T. Vhanale and A.T. Shinde, J. Iran. Chem. Soc., 19, 2641 (2022); https://doi.org/10.1007/s13738-021-02486-4
- B. Vhanale, D. Kadam and A. Shinde, Heliyon, 8, e09650 (2022); https://doi.org/10.1016/j.heliyon.2022.e09650
- J.M. Lee, S.Y. Shin, H. Yoon, M.S. Lee, Y.R. Lee, D. Koh and Y.H. Le, J. Korean Soc. Appl. Biol. Chem., 56, 343 (2013); https://doi.org/10.1007/s13765-013-3065-1
- D. Ashok, K. Padmavati, B.V. Lakshmi and M. Sarasija, Chem Heterocycl Compd., 52, 15 (2016); https://doi.org/10.1007/s10593-016-1824-8
- S.R.M. Ibrahim and G.A. Mohamed, Phytochem Rev., 15, 279 (2016); https://doi.org/10.1007/s11101-015-9413-5
- C.M. da Silva, D.L. da Silva, L.V. Modolo, R.B. Alves, M.A. de Resende, C.V.B. Martins and A. de Fa ́tima, J. Adv. Res., 2, 1 (2011); https://doi.org/10.1016/j.jare.2010.05.004
- M.S. More, P.G. Joshi, Y.K. Mishra and P.K. Khanna, Mater. Today Chem., 14, 100195 (2019); https://doi.org/10.1016/j.mtchem.2019.100195
- D.M. Boghaei and M. Lashanizadegan, Synth. Reacx. Inorg. Met.-Org. Chem., 30, 1393 (2000); https://doi.org/10.1080/00945710009351841
- D. Aggoun, M. Fernández-García, B. Bouzerafa, Y. Ouennoughi, D. López, F. Setifi and A. Ourari, Polyhedron, 187, 114640 (2020); https://doi.org/10.1016/j.poly.2020.114640
- A.A. Ardakani, H. Kargar, N. Feizi and M.N. Tahir, J. Iran. Chem. Soc., 15, 1495 (2018); https://doi.org/10.1007/s13738-018-1347-6
- S.R. Salman and F.S. Kamounah, Spectroxc Lett., 35, 327 (2002); https://doi.org/10.1081/SL-120005669
- A. Kumar, M. Agarwal and A.K. Singh, J. Organomet. Chem., 693, 3533 (2008); https://doi:10.1016/j.jorganchem.2008.07.024
- S. Chaves, A. Pérez-Redondo and R. Quevedo, J. Chem. Crystallogr., 50, 206 (2020); https://doi.org/10.1007/s10870-019-00792-7
- A. Palanimurugan and A. Kulandaisamy, Asian J. Chem., 30, 1262 (2018); https://doi.org/10.14233/ajchem.2018.21212
- K.S.A. Abou Melhaa, G.A.A. Al-Hazmib and M.S. Refat, Russ. J. Gen. Chem., 87, 3043 (2017); https://doi.org/10.1134/S1070363217120519
- P.K. Panchal, H.M. Parekh, P.B. Pansuriya and M.N. Patel, J. Enzyme Inhib. Med. Chem., 21, 203 (2006); https://doi.org/10.1080/14756360500535229
References
A. Atahan and S. Durmus, Spectrochim. Acta A Mol. Biomol., 144, 61 (2015); https://doi.org/10.1016/j.saa.2015.01.085
S. Bag, P.K. Bhaumik, S. Jana, M. Das, P. Bhowmik and S. Chattopadhyay, Polyhedron, 65, 229 (2013); https://doi.org/10.1016/j.poly.2013.08.028
B.T. Vhanale, N.J. Deshmukh and A.T. Shinde, Heliyon, 5, e02774 (2019); https://doi.org/10.1016/j.heliyon.2019.e02774
F.T. Esmadi, O.F. Khabour, K. Abbas, A.E. Mohammad, R.T. Obeidat and D. Mfady, Drug Chem Toxicol., 39, 41 (2016); https://doi.org/10.3109/01480545.2015.1017882
S. Kumar, D.N. Dhar and P.N. Saxena, J. Sci. Ind. Res., 68, 181 (2009); http://nopr.niscpr.res.in/handle/123456789/3170
Y.M. Ahmed, M.M. Omar and G.G. Mohamed, J. Iran. Chem. Soc., 19, 901 (2022); https://doi.org/10.1007/s13738-021-02359-w
M. Pal, D. Musib and M. Roy, New J. Chem., 45, 1924 (2021); https://doi.org/10.1039/D0NJ04578K
S. Makar, T. Saha and S.K. Singh, Eur. J. Med. Chem., 161, 252 (2019); https://doi.org/10.1016/j.ejmech.2018.10.018
M.A. Abozeid, A.A. El-Sawi, M. Abdelmoteleb, H. Awad, M.M. Abdel-Aziz, A.-R.H. Abdel-Rahmana and E.-S.I. El-Desoky, RSC Adv., 10, 42998 (2020); https://doi.org/10.1039/D0RA08526J
P. Pandey, A. Verma, K. Bretosh, J. Sutter and S.S. Sunkari, Polyhedron, 164, 80 (2019); https://doi.org/10.1016/j.poly.2019.02.037
A.S. Al-Bogami, A.M. Al-Majid, M.A. Al-Saad, A.A. Mousa, S.A. Al-Mazroa and H.Z. Alkhathlan, Molecules, 14, 2147 (2009); https://doi.org/10.3390/molecules14062147
C. Balakrishna, V. Kandula, R. Gudipati, S. Yennam, P.U. Devi and M. Behera, Synlett, 29, 1087 (2018); https://doi.org/10.1055/s-0036-1591898
D. Banik, J. Kuchlyan, A. Roy, N. Kundu and N. Sarkar, J. Phys. Chem. B, 119, 2310 (2015); https://doi.org/10.1021/jp5064879
S. Roy, A. Maity, N. Mudi, M. Shyamal and A. Misra, Photochem. Photobiol. Sci., 18, 1342 (2019); https://doi.org/10.1039/c8pp00558c
N. Sarkar, P.K. Bhaumik, S. Chattopadhyay, Polyhedron, 115, 37 (2016); https://doi.org/10.1016/j.poly.2016.04.013
B.T. Vhanale and A.T. Shinde, J. Iran. Chem. Soc., 19, 2641 (2022); https://doi.org/10.1007/s13738-021-02486-4
B. Vhanale, D. Kadam and A. Shinde, Heliyon, 8, e09650 (2022); https://doi.org/10.1016/j.heliyon.2022.e09650
J.M. Lee, S.Y. Shin, H. Yoon, M.S. Lee, Y.R. Lee, D. Koh and Y.H. Le, J. Korean Soc. Appl. Biol. Chem., 56, 343 (2013); https://doi.org/10.1007/s13765-013-3065-1
D. Ashok, K. Padmavati, B.V. Lakshmi and M. Sarasija, Chem Heterocycl Compd., 52, 15 (2016); https://doi.org/10.1007/s10593-016-1824-8
S.R.M. Ibrahim and G.A. Mohamed, Phytochem Rev., 15, 279 (2016); https://doi.org/10.1007/s11101-015-9413-5
C.M. da Silva, D.L. da Silva, L.V. Modolo, R.B. Alves, M.A. de Resende, C.V.B. Martins and A. de Fa ́tima, J. Adv. Res., 2, 1 (2011); https://doi.org/10.1016/j.jare.2010.05.004
M.S. More, P.G. Joshi, Y.K. Mishra and P.K. Khanna, Mater. Today Chem., 14, 100195 (2019); https://doi.org/10.1016/j.mtchem.2019.100195
D.M. Boghaei and M. Lashanizadegan, Synth. Reacx. Inorg. Met.-Org. Chem., 30, 1393 (2000); https://doi.org/10.1080/00945710009351841
D. Aggoun, M. Fernández-García, B. Bouzerafa, Y. Ouennoughi, D. López, F. Setifi and A. Ourari, Polyhedron, 187, 114640 (2020); https://doi.org/10.1016/j.poly.2020.114640
A.A. Ardakani, H. Kargar, N. Feizi and M.N. Tahir, J. Iran. Chem. Soc., 15, 1495 (2018); https://doi.org/10.1007/s13738-018-1347-6
S.R. Salman and F.S. Kamounah, Spectroxc Lett., 35, 327 (2002); https://doi.org/10.1081/SL-120005669
A. Kumar, M. Agarwal and A.K. Singh, J. Organomet. Chem., 693, 3533 (2008); https://doi:10.1016/j.jorganchem.2008.07.024
S. Chaves, A. Pérez-Redondo and R. Quevedo, J. Chem. Crystallogr., 50, 206 (2020); https://doi.org/10.1007/s10870-019-00792-7
A. Palanimurugan and A. Kulandaisamy, Asian J. Chem., 30, 1262 (2018); https://doi.org/10.14233/ajchem.2018.21212
K.S.A. Abou Melhaa, G.A.A. Al-Hazmib and M.S. Refat, Russ. J. Gen. Chem., 87, 3043 (2017); https://doi.org/10.1134/S1070363217120519
P.K. Panchal, H.M. Parekh, P.B. Pansuriya and M.N. Patel, J. Enzyme Inhib. Med. Chem., 21, 203 (2006); https://doi.org/10.1080/14756360500535229