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Synthesis, Characterization and Biological Studies on Cobalt(II) and Nickel(II) Complexes with Mannich Base 2-(Pyrrolidin-1-ylmethyl)isoindoline-1,3-dione
Corresponding Author(s) : M. Yosuva Suvaikin
Asian Journal of Chemistry,
Vol. 31 No. 7 (2019): Vol 31 Issue 7
Abstract
A new Mannich base 2-(pyrrolidin-1-ylmethyl)isoindoline-1,3-dione was synthesized by the condensation of phthalimide, formaldehyde and pyrrolidine and was characterized on the basis of elemental analysis and IR, UV-visible, 1H and 13C NMR data. Cobalt(II) and nickel(II) complexes of new Mannich base were synthesized and characterized by elemental analysis, electrical conductance, electronic and IR spectra, magnetic measurements, thermal analysis and cyclic voltammetric studies. From IR data, it is inferred that the ligand is neutral bidentate bonding through pyrrolidine ring containing nitrogen and one of the two carbonyl oxygens. The magnetic moment values and electronic spectral data show that all the complexes studied are tetrahedral except Co(II) chloro complex. The electrochemical studies show that Co(II)/Co(I) redox couple exists during electrolysis. Thermal results indicate that Co(II) sulphato and Ni(II) chloro complexes undergo two stage decompositions to produce CoSO4 and NiO, respectively as final residues and that the ligand forms a polymer of formaldehyde as an intermediate. The antimicrobial activity measured by the agar well diffusion method showed that the metal complexes are more active than the ligand probably because of the chelation effect.
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- V. Cechinel Filho, F. Campos, R. Corrêa, R.A. Yunes and R.J. Nunes, Quim. Nova, 26, 230 (2003); https://doi.org/10.1590/S0100-40422003000200016.
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References
V. Cechinel Filho, F. Campos, R. Corrêa, R.A. Yunes and R.J. Nunes, Quim. Nova, 26, 230 (2003); https://doi.org/10.1590/S0100-40422003000200016.
F. Hassazadeh, M. Rabbani, G.A. Khodarahmi, G.H. Hakimelalahi, A. Fasihi and M. Mohajeri, Res. Pharm. Sci., 2, 35 (2007).
S.M. Sami, R.T. Dorr, D.S. Alberts, A.M. Sólyom and W.A. Remers, J. Med. Chem., 43, 3067 (2000); https://doi.org/10.1021/jm9905817.
J.A. Yunes, A.A. Cardoso, R.A. Yunes, R. Corrêa, F. de Campos-Buzzi and V.C. Filho, Z. Naturforsch. C, 63, 675 (2008); https://doi.org/10.1515/znc-2008-9-1011.
S.P. Mahapatra, P. Ghode, D.K. Jain, S.C. Chaturvedi, B.C. Maiti and T.K. Maity, J. Pharm. Sci. Res., 2, 567 (2010).
X. Collin, J.-M. Robert, G. Wielgosz, G. Le Baut, C. Bobin-Dubigeon, N. Grimaud and J.-Y. Petit, Eur. J. Med. Chem., 36, 639 (2001); https://doi.org/10.1016/S0223-5234(01)01254-5.
S. Kawaguchi and O. Ikeda, Jpn. Pat. Appl. JP2001328911 (2001).
K. Ebihara, T. Oora, M. Nakaya, S. Shiraishi and N. Yasui, Jpn. Pat. Appl. JP08245585 (1996).
C.S. Chidan Kumar, W.-S. Loh, S. Chandraju, Y.-F. Win, W.K. Tan C.K. Quah and H.-K. Fun, PLoS ONE, 10, e0119440 (2015); https://doi.org/10.1371/journal.pone.0119440.
A.J. Abdulghani and N.M. Abbas, Bioinorg. Chem. Appl., 2011, Article ID 706262 (2011); https://doi.org/10.1155/2011/706262.
A.A. Raj, R. Raghunathan, M.R. Sridevi Kumari and N. Raman, Bioorg. Med. Chem., 11, 407 (2003); https://doi.org/10.1016/S0968-0896(02)00439-X.
I. Stylianakis, A. Kolocouris, N. Kolocouris, G. Fytas, G.B. Foscolos, E. Padalko, J. Neyts and E. De Clercq, Bioorg. Med. Chem. Lett., 13, 1699 (2003); https://doi.org/10.1016/S0960-894X(03)00231-2.
J. Obniska, S. Jurczyk, A. Zejc, K. Kaminiski, E. Tatarcynska and K. Stachowicz, Pharmacol. Rep., 57, 170 (2005).
J. Obniska and A. Zagorska, Farmaco, 58, 1227 (2003); https://doi.org/10.1016/S0014-827X(03)00187-3.
N. Kolocouris, G.B. Foscolos, A. Kolocouris, P. Marakos, N. Pouli, G. Fytas, S. Ikeda and E. De Clercq, J. Med. Chem., 37, 2896 (1994); https://doi.org/10.1021/jm00044a010.
M.R. Abdullahi and S. Rajeswari, Proceedings, Article No. 1106856 (2016).
D. Tamilvendan, S. Rajeswari, S. Ilavenil and G.V Prabhu, Orbital Elec. J. Chem., 2, 10 (2010).
M. Ramesh, Ph.D. Thesis, Synthesis, Characterization and Antimicrobial Studies on Metal Complexes of New Mannich Bases Derived from Phthalimide and Succinimide, Bharathidasan University, Tiruchirappalli, India (2011).
J. Bassett, R.C. Denney, G.H. Jeffery and J. Hendham, Vogel’s Text Book of Quantiative Analysis, ELBS: Longman, edn 4 (1986).
A. Earnshaw, Introduction to Magneto-Chemistry, Academic Press: New York (1968).
A.J. Bard and L.R. Isata, Electrochemical Methods: Fundamentals and Applications, John Wiley & Sons: USA (1980).
R.M. Silverstein and F.X. Webster, Spectrometric Identification of Organic Compounds, John Wiley & Sons Inc.: New York, edn 6 (1997).
L.J. Bellamy, The Infrared Spectra of Complex Molecules, Methuer: London, edn 2 (1958).
P. Sakthivel, P.S. Joseph, A. Sebastiyan, M.Y. Suvaikin and M. Ramesh, Acta Crystallogr. Sect. E Struct. Rep. Online, 63, o4388 (2007); https://doi.org/10.1107/S1600536807050519.
G. Shankar, P.S. Joseph, M. Yosuva Suvakin and A. Sebastiyan, Physica B, 405, 4231 (2010); https://doi.org/10.1016/j.physb.2010.07.016.
W.J. Geary, Coord. Chem. Rev., 7, 81 (1971); https://doi.org/10.1016/S0010-8545(00)80009-0.
H. Adams, N. Bailey, T.N. Briggs, J.A. McCleverty, H.M. Colquhoun and D.J. Williams, J. Chem. Soc., Dalton Trans., 813 (1986); https://doi.org/10.1039/DT9860000813.
I.J.S. Fairlamb, A.R. Kapdi, A.F. Lee, G. Sanchez, G. Lopez, J.L. Serrano, L. Garcia, J. Perez and E. Perez, J. Chem. Soc., Dalton Trans., 3970 (2004); https://doi.org/10.1039/B413886D.
J.R. Ferraro, Low Frequency Vibrations of Inorganic and Coordination Compounds, Plenum Press: New York (1971).
K. Nakamato, Infrared and Raman Spectra of Inorganic and Coordination Compounds, Wiley Interscience: New York, edn 3, p. 156 (1978).
D.M.L. Goodgame, M. Goodgame and F.A. Cotton, J. Am. Chem. Soc., 83, 4161 (1961); https://doi.org/10.1021/ja01481a014.
A.B.P. Lever, Inorganic Electronic Spectroscopy, Elsevier: Amsterdam (1968).
B.N. Figgis and J. Lewis, Progress in Inorganic Chemistry, Interscience: New York, vol. 6 (1964).
L. Sacconi, J. Am. Chem. Soc., 76, 3400 (1954); https://doi.org/10.1021/ja01642a012.
H. Arslan, N.O. Pozan and N. Tarkan, Thermochim. Acta, 383, 69 (2002); https://doi.org/10.1016/S0040-6031(01)00657-8.
A.D. Kulkarni, S.A. Patil and P.S. Badami, Int. J. Electrochem. Sci., 4, 717 (2009).
R.S. Joseyphus and M.S. Nair, Arab. J. Chem., 3, 195 (2010); https://doi.org/10.1016/j.arabjc.2010.05.001.