Copyright (c) 2021 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Bioactive Metal Complexes of Schiff Base Derived from 2,3-Dioxobutane, Ethane-1,2-diamine and 4-Chloro-2-formylphenol: Spectral Studies and in vitro Antimicrobial Activity
Corresponding Author(s) : Abhay Nanda srivastava
Asian Journal of Chemistry,
Vol. 33 No. 12 (2021): Vol 33 Issue 12, 2021
Abstract
A novel series of trivalent coordination complexes was synthesized by the reaction between a chloride/acetate salt of iron, chromium, cobalt or manganese ions and NNNNOO type persuasive Schiff base ligand synthesized from 2,3-dioxobutane, ethane-1,2-diamine and 4-chloro-2-formylphenol. Synthesized compounds were characterized by using elemental analysis, molar conductance, magnetic moment, IR, UV-visible, 1H NMR, 13C NMR and ESI-MS spectral analyses. IR and NMR spectra favoured hexadentate coordination behaviour of ligand. Electronic spectra and magnetic moment data reveal Oh geometry with distortion around the metal ion in complexes. The molar conductance values show 1:1 electrolytic nature of complexes. Biological potentiality of the ligand and its metal complexes were tested in vitro against two bacterial and two fungal strains; Bacillus subtilis, Escherichia coli and Aspirgillus niger, Aspirgillus flavus, respectively.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- S.H. Sumrra, I. Sahrish, M.A. Raza, Z. Ahmad, M.N. Zafar, Z.H. Chohan, M. Khalid and S. Ahmed, Monatsh. Chem., 151, 549 (2020); https://doi.org/10.1007/s00706-020-02571-z
- R.D. Hancock and A.E. Martell, Chem. Rev., 89, 1875 (1989); https://doi.org/10.1021/cr00098a011
- H. Kargar, A.A. Ardakani, M.N. Tahir, M. Ashfaq and K.S. Munawar, J. Mol. Struct., 1229, 129842 (2021); https://doi.org/10.1016/j.molstruc.2020.129842
- D. Aggoun, Z. Messasma, B. Bouzerafa, R. Berenguer, E. Morallon, Y. Ouennoughi and A. Ourari, J. Mol. Struct., 1231, 129923 (2021); https://doi.org/10.1016/j.molstruc.2021.129923
- A.A. El-Sherif and M.S. Aljahdali, J. Coord. Chem., 66, 3423 (2013); https://doi.org/10.1080/00958972.2013.839027
- M. Manimohan, S. Pugalmani and M.A. Sithique, Int. J. Biol. Macromol., 136, 738 (2019); https://doi.org/10.1016/j.ijbiomac.2019.06.115
- P. Mucha, P. Hikisz, K. Gwozdzinski, U. Krajewska, A. Leniart and E. Budzisz, RSC Adv., 9, 31943 (2019); https://doi.org/10.1039/C9RA05971G
- J.L. Sessler, T.D. Mody, G.W. Hemmi, V. Lynch, S.W. Young and R.A. Miller, J. Am. Chem. Soc., 115, 10368 (1993); https://doi.org/10.1021/ja00075a066
- A.H. Ismail, B.H. Al-Zaidi, A.N. Abd and N.F. Habubi, Chem. Pap., 74, 2069 (2020); https://doi.org/10.1007/s11696-019-01007-1
- Y. Sun, Y. Lu, M. Bian, Z. Yang, X. Ma and W. Liu, Eur. J. Med. Chem., 211, 113098 (2021); https://doi.org/10.1016/j.ejmech.2020.113098
- N. Patel, A.K. Prajapati, R.N. Jadeja, R.N. Patel, S.K. Patel, I.P. Tripathi, N. Dwivedi, V.K. Gupta and R.J. Butcher, Polyhedron, 180, 114434 (2020); https://doi.org/10.1016/j.poly.2020.114434
- G. Kapoor, D.P. Pathak, R. Bhutani, A. Husain, S. Jain and M.A. Iqbal, Bioorg. Chem., 84, 478 (2019); https://doi.org/10.1016/j.bioorg.2018.12.004
- D.M. Yufanyi, H.S. Abbo, S.J.J. Titinchi and T. Neville, Coord. Chem. Rev., 414, 213285 (2020); https://doi.org/10.1016/j.ccr.2020.213285
- 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
- T.B. Hadda, M. Akkurt, M.F. Baba, M. Daoudi, B. Bennani, A. Kerbal and Z.H. Chohan, J. Enzyme Inhib. Med. Chem., 24, 457 (2009); https://doi.org/10.1080/14756360802188628
- M. Carcelli, D. Rogolino, M. Sechi, G. Rispoli, E. Fisicaro, C. Compari, N. Grandi, A. Corona, E. Tramontano, C. Pannecouque and L. Naesens, Eur. J. Med. Chem., 83, 594 (2014); https://doi.org/10.1016/j.ejmech.2014.06.055
- F. Aghvami, A. Ghaffari, M. Kucerakova, M. Dusek, R. Karimi-Nami, M. Amini and M. Behzad, Polyhedron, 200, 115135 (2021); https://doi.org/10.1016/j.poly.2021.115135
- Y.P.A. Torres, Ligands and coordination compounds used as new photosensitized materials for the construction of solar cells, in Stability and Applications of Coordination Compounds, ed. by A.N. Srivastva, (IntechOpen, U.K., 2020), p.119-142. https://doi.org/10.5772/intechopen.92268
- M.A. Sahudin, L.L. Tan, M.S. Su’ait, N.H.A. Karim and M.M. Mackeen, Electrochim. Acta, 379, 138186 (2021); https://doi.org/10.1016/j.electacta.2021.138186
- A. Kumar, N.P. Singh, M. Kumar and U. Agarwal, Drug Res., 71, 317 (2021); https://doi.org/10.1055/a-1302-7649
- A.A. Jadhav, V.P. Dhanwe and P.K. Khanna, Polyhedron, 123, 99 (2017); https://doi.org/10.1016/j.poly.2016.10.039
- J. Singh, A.N. Srivastav, N.P. Singh and A. Singh, Stability of Metal Complexes in solution, in Stability and Applications of Coordination Compounds, IntechOpen, U.K., pp. 41-58 (2020). https://doi.org/10.5772/intechopen.90183
- A. Trehoux, J.P. Mahy and F. Avenier, Coord. Chem. Rev., 322, 142 (2016); https://doi.org/10.1016/j.ccr.2016.05.014
- J. Yuan, X. Wang, M.J. Liu and H.Z. Kou, Inorg. Chim. Acta, 449, 69 (2016); https://doi.org/10.1016/j.ica.2016.04.034
- B.J. Langford, M. So, S. Raybardhan, V. Leung, D. Westwood, D.R. MacFadden, J.P.R. Soucy and N. Daneman, Clin. Microbiol. Infect., 26, 1622 (2020); https://doi.org/10.1016/j.cmi.2020.07.016
- M.J. Cox, N. Loman, D. Bogaert and J. O’Grady, Lancet Microbe, 1, E11 (2020); https://doi.org/10.1016/S2666-5247(20)30009-4
- G. Song, G. Liang and W. Liu, Mycopathologia, 185, 599 (2020); https://doi.org/10.1007/s11046-020-00462-9
- E. Sieswerda, M.G.J. de Boer, M.M.J. Bonten, W.G. Boersma, R.E. Jonkers, R.M. Aleva, B.J. Kullberg, J.A. Schouten, E.M.W. van de Garde, T.J. Verheij, M.M. van der Eerden, J.M. Prins and W.J. Wiersinga, Clin. Microbiol. Infect., 27, 61 (2021); https://doi.org/10.1016/j.cmi.2020.09.041
- E. Brown and G. Wright, Nature, 529, 336 (2016); https://doi.org/10.1038/nature17042
- A. Frei, J. Zuegg, A.G. Elliott, M. Baker, S. Braese, C. Brown, F. Chen, C. G. Dowson, G. Dujardin, N. Jung, A.P. King, A.M. Mansour, M. Massi, J. Moat, H.A. Mohamed, A.K. Renfrew, P.J. Rutledge, P.J. Sadler, M.H. Todd, C.E. Willans, J.J. Wilson, M.A. Cooper and M.A.T. Blaskovich, Chem. Sci., 11, 2627 (2020); https://doi.org/10.1039/C9SC06460E
- W. Guerra, P.P. Silva-Caldeira, H. Terenzi and E.C. Pereira-Maia, Coord. Chem. Rev., 327–328, 188 (2016); https://doi.org/10.1016/j.ccr.2016.04.009
- M. Pervaiz, A. Riaz, A. Munir, Z. Saeed, S. Hussain, A. Rashid, U. Younas and A. Adnan, J. Mol. Struct., 1202, 127284 (2020); https://doi.org/10.1016/j.molstruc.2019.127284
- A.I. Vogel, A Text Book of Quantitative Inorganic Analysis, Logmans: London p. 433 (1961).
- A.K. Sadana, Y. Mirza, K.R. Aneja and O. Prakash, Eur. J. Med. Chem., 38, 533 (2003); https://doi.org/10.1016/S0223-5234(03)00061-8
- W.J. Geary, Coord. Chem. Rev., 7, 81 (1971); https://doi.org/10.1016/S0010-8545(00)80009-0
- A.N. Srivastva, N.P. Singh and C.K. Shriwastaw, Res. Chem. Intermed., 43, 3663 (2017); https://doi.org/10.1007/s11164-016-2839-6
- K. Nakamoto, Infrared and Raman Spectra of Inorganic and Coordination Compounds, Part A: Theory and applications in Inorganic Chemistry, John Wiley and Sons Ltd., USA, Edn.: 6 (2006).
- T. Chowdhury, S. Chatterjee, P. Banerjee, D. Sukul, M. Shukla and T. Chattopadhyay, J. Coord. Chem., 73, 754 (2020); https://doi.org/10.1080/00958972.2020.1749273
- A.N. Srivastva, N.P. Singh and C.K. Shriwastaw, Arab. J. Chem., 9, 48 (2016); https://doi.org/10.1016/j.arabjc.2014.10.004
- A.N. Srivastva, S.C. Pahwa, P.C. Jain and N.P. Singh, Res. Chem. Intermed., 42, 8023 (2016); https://doi.org/10.1007/s11164-016-2576-x
- V.A. Shelke, S.M. Jadhav, V.R. Patharkar, S.G. Shankarwar, A.S. Munde and T.K. Chondhekar, Arab. J. Chem., 5, 501 (2012); https://doi.org/10.1016/j.arabjc.2010.09.018
- M.A. Neelakantan, S.S. Marriappan, J. Dharmaraja, T. Jeyakumar, K. Muthukumaran and X.R.D. Spectral, Spectrochim. Acta A Mol. Biomol. Spectrosc., 71, 628 (2008); https://doi.org/10.1016/j.saa.2008.01.023
- N.P. Singh and A.N. Srivastava, Asian J. Chem., 25, 533 (2013); https://doi.org/10.14233/ajchem.2013.13484
- N.P. Singh and A.N. Srivastava, J. Serb. Chem. Soc., 77, 627 (2012); https://doi.org/10.2298/JSC110412148S
- A.B.P. Lever, Inorganic Electronic Spectroscopy, Elsevier: New York, Edn.: 2, p. 420 (1968).
- C.M. Sharaby, G.G. Mohamed and M.M. Omar, Spectrochim. Acta A Mol. Biomol. Spectrosc., 66, 935 (2007); https://doi.org/10.1016/j.saa.2006.04.032
- B.T. Thaker, J. Lekhadia, A. Patel and P. Thaker, Transition Met. Chem., 19, 623 (1994); https://doi.org/10.1007/BF00980417
- D.J. Radanovic, M.I. Djuran, T.S. Kostic, C. Maricondi and B.E. Douglas, Inorg. Chim. Acta, 207, 111 (1993); https://doi.org/10.1016/S0020-1693(00)91463-4
- V.K. Sharma and S. Srivastava, J. Coord. Chem., 61, 178 (2008); https://doi.org/10.1080/00958970701318426
- S.N. Sovari and F. Zobi, Chemistry, 2, 418 (2020); https://doi.org/10.3390/chemistry2020026
References
S.H. Sumrra, I. Sahrish, M.A. Raza, Z. Ahmad, M.N. Zafar, Z.H. Chohan, M. Khalid and S. Ahmed, Monatsh. Chem., 151, 549 (2020); https://doi.org/10.1007/s00706-020-02571-z
R.D. Hancock and A.E. Martell, Chem. Rev., 89, 1875 (1989); https://doi.org/10.1021/cr00098a011
H. Kargar, A.A. Ardakani, M.N. Tahir, M. Ashfaq and K.S. Munawar, J. Mol. Struct., 1229, 129842 (2021); https://doi.org/10.1016/j.molstruc.2020.129842
D. Aggoun, Z. Messasma, B. Bouzerafa, R. Berenguer, E. Morallon, Y. Ouennoughi and A. Ourari, J. Mol. Struct., 1231, 129923 (2021); https://doi.org/10.1016/j.molstruc.2021.129923
A.A. El-Sherif and M.S. Aljahdali, J. Coord. Chem., 66, 3423 (2013); https://doi.org/10.1080/00958972.2013.839027
M. Manimohan, S. Pugalmani and M.A. Sithique, Int. J. Biol. Macromol., 136, 738 (2019); https://doi.org/10.1016/j.ijbiomac.2019.06.115
P. Mucha, P. Hikisz, K. Gwozdzinski, U. Krajewska, A. Leniart and E. Budzisz, RSC Adv., 9, 31943 (2019); https://doi.org/10.1039/C9RA05971G
J.L. Sessler, T.D. Mody, G.W. Hemmi, V. Lynch, S.W. Young and R.A. Miller, J. Am. Chem. Soc., 115, 10368 (1993); https://doi.org/10.1021/ja00075a066
A.H. Ismail, B.H. Al-Zaidi, A.N. Abd and N.F. Habubi, Chem. Pap., 74, 2069 (2020); https://doi.org/10.1007/s11696-019-01007-1
Y. Sun, Y. Lu, M. Bian, Z. Yang, X. Ma and W. Liu, Eur. J. Med. Chem., 211, 113098 (2021); https://doi.org/10.1016/j.ejmech.2020.113098
N. Patel, A.K. Prajapati, R.N. Jadeja, R.N. Patel, S.K. Patel, I.P. Tripathi, N. Dwivedi, V.K. Gupta and R.J. Butcher, Polyhedron, 180, 114434 (2020); https://doi.org/10.1016/j.poly.2020.114434
G. Kapoor, D.P. Pathak, R. Bhutani, A. Husain, S. Jain and M.A. Iqbal, Bioorg. Chem., 84, 478 (2019); https://doi.org/10.1016/j.bioorg.2018.12.004
D.M. Yufanyi, H.S. Abbo, S.J.J. Titinchi and T. Neville, Coord. Chem. Rev., 414, 213285 (2020); https://doi.org/10.1016/j.ccr.2020.213285
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
T.B. Hadda, M. Akkurt, M.F. Baba, M. Daoudi, B. Bennani, A. Kerbal and Z.H. Chohan, J. Enzyme Inhib. Med. Chem., 24, 457 (2009); https://doi.org/10.1080/14756360802188628
M. Carcelli, D. Rogolino, M. Sechi, G. Rispoli, E. Fisicaro, C. Compari, N. Grandi, A. Corona, E. Tramontano, C. Pannecouque and L. Naesens, Eur. J. Med. Chem., 83, 594 (2014); https://doi.org/10.1016/j.ejmech.2014.06.055
F. Aghvami, A. Ghaffari, M. Kucerakova, M. Dusek, R. Karimi-Nami, M. Amini and M. Behzad, Polyhedron, 200, 115135 (2021); https://doi.org/10.1016/j.poly.2021.115135
Y.P.A. Torres, Ligands and coordination compounds used as new photosensitized materials for the construction of solar cells, in Stability and Applications of Coordination Compounds, ed. by A.N. Srivastva, (IntechOpen, U.K., 2020), p.119-142. https://doi.org/10.5772/intechopen.92268
M.A. Sahudin, L.L. Tan, M.S. Su’ait, N.H.A. Karim and M.M. Mackeen, Electrochim. Acta, 379, 138186 (2021); https://doi.org/10.1016/j.electacta.2021.138186
A. Kumar, N.P. Singh, M. Kumar and U. Agarwal, Drug Res., 71, 317 (2021); https://doi.org/10.1055/a-1302-7649
A.A. Jadhav, V.P. Dhanwe and P.K. Khanna, Polyhedron, 123, 99 (2017); https://doi.org/10.1016/j.poly.2016.10.039
J. Singh, A.N. Srivastav, N.P. Singh and A. Singh, Stability of Metal Complexes in solution, in Stability and Applications of Coordination Compounds, IntechOpen, U.K., pp. 41-58 (2020). https://doi.org/10.5772/intechopen.90183
A. Trehoux, J.P. Mahy and F. Avenier, Coord. Chem. Rev., 322, 142 (2016); https://doi.org/10.1016/j.ccr.2016.05.014
J. Yuan, X. Wang, M.J. Liu and H.Z. Kou, Inorg. Chim. Acta, 449, 69 (2016); https://doi.org/10.1016/j.ica.2016.04.034
B.J. Langford, M. So, S. Raybardhan, V. Leung, D. Westwood, D.R. MacFadden, J.P.R. Soucy and N. Daneman, Clin. Microbiol. Infect., 26, 1622 (2020); https://doi.org/10.1016/j.cmi.2020.07.016
M.J. Cox, N. Loman, D. Bogaert and J. O’Grady, Lancet Microbe, 1, E11 (2020); https://doi.org/10.1016/S2666-5247(20)30009-4
G. Song, G. Liang and W. Liu, Mycopathologia, 185, 599 (2020); https://doi.org/10.1007/s11046-020-00462-9
E. Sieswerda, M.G.J. de Boer, M.M.J. Bonten, W.G. Boersma, R.E. Jonkers, R.M. Aleva, B.J. Kullberg, J.A. Schouten, E.M.W. van de Garde, T.J. Verheij, M.M. van der Eerden, J.M. Prins and W.J. Wiersinga, Clin. Microbiol. Infect., 27, 61 (2021); https://doi.org/10.1016/j.cmi.2020.09.041
E. Brown and G. Wright, Nature, 529, 336 (2016); https://doi.org/10.1038/nature17042
A. Frei, J. Zuegg, A.G. Elliott, M. Baker, S. Braese, C. Brown, F. Chen, C. G. Dowson, G. Dujardin, N. Jung, A.P. King, A.M. Mansour, M. Massi, J. Moat, H.A. Mohamed, A.K. Renfrew, P.J. Rutledge, P.J. Sadler, M.H. Todd, C.E. Willans, J.J. Wilson, M.A. Cooper and M.A.T. Blaskovich, Chem. Sci., 11, 2627 (2020); https://doi.org/10.1039/C9SC06460E
W. Guerra, P.P. Silva-Caldeira, H. Terenzi and E.C. Pereira-Maia, Coord. Chem. Rev., 327–328, 188 (2016); https://doi.org/10.1016/j.ccr.2016.04.009
M. Pervaiz, A. Riaz, A. Munir, Z. Saeed, S. Hussain, A. Rashid, U. Younas and A. Adnan, J. Mol. Struct., 1202, 127284 (2020); https://doi.org/10.1016/j.molstruc.2019.127284
A.I. Vogel, A Text Book of Quantitative Inorganic Analysis, Logmans: London p. 433 (1961).
A.K. Sadana, Y. Mirza, K.R. Aneja and O. Prakash, Eur. J. Med. Chem., 38, 533 (2003); https://doi.org/10.1016/S0223-5234(03)00061-8
W.J. Geary, Coord. Chem. Rev., 7, 81 (1971); https://doi.org/10.1016/S0010-8545(00)80009-0
A.N. Srivastva, N.P. Singh and C.K. Shriwastaw, Res. Chem. Intermed., 43, 3663 (2017); https://doi.org/10.1007/s11164-016-2839-6
K. Nakamoto, Infrared and Raman Spectra of Inorganic and Coordination Compounds, Part A: Theory and applications in Inorganic Chemistry, John Wiley and Sons Ltd., USA, Edn.: 6 (2006).
T. Chowdhury, S. Chatterjee, P. Banerjee, D. Sukul, M. Shukla and T. Chattopadhyay, J. Coord. Chem., 73, 754 (2020); https://doi.org/10.1080/00958972.2020.1749273
A.N. Srivastva, N.P. Singh and C.K. Shriwastaw, Arab. J. Chem., 9, 48 (2016); https://doi.org/10.1016/j.arabjc.2014.10.004
A.N. Srivastva, S.C. Pahwa, P.C. Jain and N.P. Singh, Res. Chem. Intermed., 42, 8023 (2016); https://doi.org/10.1007/s11164-016-2576-x
V.A. Shelke, S.M. Jadhav, V.R. Patharkar, S.G. Shankarwar, A.S. Munde and T.K. Chondhekar, Arab. J. Chem., 5, 501 (2012); https://doi.org/10.1016/j.arabjc.2010.09.018
M.A. Neelakantan, S.S. Marriappan, J. Dharmaraja, T. Jeyakumar, K. Muthukumaran and X.R.D. Spectral, Spectrochim. Acta A Mol. Biomol. Spectrosc., 71, 628 (2008); https://doi.org/10.1016/j.saa.2008.01.023
N.P. Singh and A.N. Srivastava, Asian J. Chem., 25, 533 (2013); https://doi.org/10.14233/ajchem.2013.13484
N.P. Singh and A.N. Srivastava, J. Serb. Chem. Soc., 77, 627 (2012); https://doi.org/10.2298/JSC110412148S
A.B.P. Lever, Inorganic Electronic Spectroscopy, Elsevier: New York, Edn.: 2, p. 420 (1968).
C.M. Sharaby, G.G. Mohamed and M.M. Omar, Spectrochim. Acta A Mol. Biomol. Spectrosc., 66, 935 (2007); https://doi.org/10.1016/j.saa.2006.04.032
B.T. Thaker, J. Lekhadia, A. Patel and P. Thaker, Transition Met. Chem., 19, 623 (1994); https://doi.org/10.1007/BF00980417
D.J. Radanovic, M.I. Djuran, T.S. Kostic, C. Maricondi and B.E. Douglas, Inorg. Chim. Acta, 207, 111 (1993); https://doi.org/10.1016/S0020-1693(00)91463-4
V.K. Sharma and S. Srivastava, J. Coord. Chem., 61, 178 (2008); https://doi.org/10.1080/00958970701318426
S.N. Sovari and F. Zobi, Chemistry, 2, 418 (2020); https://doi.org/10.3390/chemistry2020026