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Synthesis of Schiff Base (E)-2-(((3-Hydroxyphenyl)imino)methyl)-6-methoxyphenol Containing N and O Donors and its Metal Complexes: Spectral, Thermal, Redox Behaviour, Fluorescence Quenching, Antimicrobial and Anticancer Studies
Corresponding Author(s) : G. Valarmathy
Asian Journal of Chemistry,
Vol. 30 No. 3 (2018): Vol 30 Issue 3
Abstract
Convenient synthesis of new octahedral complexes from 3-aminophenol and 2-hydroxy-3-methoxybenzaldehyde with the molecular formula [M(L2-2H)] (where M = Mn2+ and Co2+) have been described. The Schiff base behaves as a tridentate ligand with O and N donors and coordinates to metal ion via phenolic oxygens and azomethine nitrogen. The compositions of the ligand and its metal complexes have been established by elemental analysis and metal estimation. The ionic nature of the metal complexes has been deduced from conductance measurements. Structural features and bonding mode of Schiff base have been proposed by magnetic properties and spectral methods. Both the complexes exhibit d-d transitions, photo emissive and redox behaviour. The Schiff base ligand and its metal complexes have been screened for antimicrobial evaluation towards some clinically important microorganisms. The quenching studies were carried out for the [Co(L2-2H)] complex by alizarin red S dye in DMSO using fluorescence measurements. The evaluated highly biologically active [Co(L2-2H)] complex shows excellent cytotoxicity towards (MCF-7) cancer cell line.
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- L. Mishra and S. Ragini, Indian J. Chem., 29A, 1131 (2000).
- J. Mannad and J.C. Crabbe, Bacterial and Antibacterial Agents, Spectrum Academic Publishers, Oxford (1996).
- A.M. Abu-Dief, I.M.A. Mohamed, Beni-Suef Univ. J. Basic Appl. Sci., 4, 119 (2015); https://doi.org/10.1016/j.bjbas.2015.05.004.
- G. Valarmathy and R. Subbalakshmi, Asian J. Chem., 25, 2077 (2013); https://doi.org/10.14233/ajchem.2013.13322.
- R.K. Dubey, J. Indian Chem. Soc., 83, 1087 (2006).
- P.S. Reddyb B. Satyanarayana and Jayatyagaraju, J. Indian Chem. Soc., 83, 1204 (2006).
- B.T. Thaker and R.S. Barvalia, J. Coord. Chem., 63, 1597 (2000); https://doi.org/10.1080/00958972.2010.483767.
- V. Govindaraj and S. Ramanathan, Turk. J. Chem., 38, 521 (2014); https://doi.org/10.3906/kim-1301-83.
- V. Gomathi, R. Selvameena, R. Subbalakshmi and G. Valarmathy, Orient. J. Chem., 29, 533 (2013); https://doi.org/10.13005/ojc/290220.
- G. Valarmathy and R. Subbalakshmi, Indian J. Appl. Res., 3, 43 (2013); https://doi.org/10.15373/2249555X/APR2013/14.
- P.C.S. Rani, L. R.K and G.S. Thara, Orient. J. Chem., 29, 315 (2013); https://doi.org/10.13005/ojc/290151.
- G. Valarmathy and R. Subbalakshmi, Int. J. Pharm. Pharm. Sci., 5, 368 (2013).
- W.J. Geary, Coord. Chem. Rev., 7, 81 (1971); https://doi.org/10.1016/S0010-8545(00)80009-0.
- L.N. Sharda and M.C. Ganokar, Indian J. Chem., 27A, 617 (1988).
- P. Chattopadhyay and C. Sinha, Indian J. Chem., 34A, 76 (1995).
- T.R. Rao, S. Shrestha, A. Prasad and K.K. Narang, Synth. React. Inorg. Met.-Org. Chem., 32, 419 (2002); https://doi.org/10.1081/SIM-120003216.
- R.C. Maurya and P. Patel, Spec. Lett., 32, 213 (1999); https://doi.org/10.1080/00387019909349979.
- P.P. Bhargava, R. Bembi and M. Tyagi, J. Indian Chem. Soc., 60, 214 (1983).
- R.C. Maurya, D.D. Mishra, S. Mukherjee and J. Dubey, Polyhedron, 14, 1351 (1995); https://doi.org/10.1016/0277-5387(94)00394-T.
- J.D. Lee, Concise Inorganic Chemistry, Blackwell Science Publishers, edn 5, p. 967, (1999).
- H.R. Singh and B.V. Agarwala, J. Indian Chem. Soc., 65, 591 (1988).
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- D.J. Pasto, Organic Structure Determination, Prentice Hall, International, London (1969).
- Z.H. Chohan and M.M. Naseer, Appl. Organomet. Chem., 21, 728 (2007); https://doi.org/10.1002/aoc.1279.
- G.A. Mabbot, J. Chem. Educ., 60, 697 (1983); https://doi.org/10.1021/ed060p697.
- Indian Pharmacopoeia, IIA, 105 (1996).
- R. Cruickshank, J.O. Dugid, B.P. Marnion and R.H. Swain, Medical Microbiology, Churchill Livingston Publication, New York, edn 12, vol. II, p. 98 (1975).
- T. Mosmann, J. Immunol. Methods, 65, 55 (1983); https://doi.org/10.1016/0022-1759(83)90303-4.
- M. Navarra, M. Celano, J. Maiuolo, S. Schenone, M. Botta, A. Angelucci, P. Bramanti and D. Russo, BMC Cancer, 10, 602 (2010); https://doi.org/10.1186/1471-2407-10-602.
- H.R. Park, C.H. Oh, H.C. Lee, J.G. Choi, B.I. Jung and K.M. Bark, Bull. Korean Chem. Soc., 27, 2002 (2006); https://doi.org/10.5012/bkcs.2006.27.12.2002.
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References
L. Mishra and S. Ragini, Indian J. Chem., 29A, 1131 (2000).
J. Mannad and J.C. Crabbe, Bacterial and Antibacterial Agents, Spectrum Academic Publishers, Oxford (1996).
A.M. Abu-Dief, I.M.A. Mohamed, Beni-Suef Univ. J. Basic Appl. Sci., 4, 119 (2015); https://doi.org/10.1016/j.bjbas.2015.05.004.
G. Valarmathy and R. Subbalakshmi, Asian J. Chem., 25, 2077 (2013); https://doi.org/10.14233/ajchem.2013.13322.
R.K. Dubey, J. Indian Chem. Soc., 83, 1087 (2006).
P.S. Reddyb B. Satyanarayana and Jayatyagaraju, J. Indian Chem. Soc., 83, 1204 (2006).
B.T. Thaker and R.S. Barvalia, J. Coord. Chem., 63, 1597 (2000); https://doi.org/10.1080/00958972.2010.483767.
V. Govindaraj and S. Ramanathan, Turk. J. Chem., 38, 521 (2014); https://doi.org/10.3906/kim-1301-83.
V. Gomathi, R. Selvameena, R. Subbalakshmi and G. Valarmathy, Orient. J. Chem., 29, 533 (2013); https://doi.org/10.13005/ojc/290220.
G. Valarmathy and R. Subbalakshmi, Indian J. Appl. Res., 3, 43 (2013); https://doi.org/10.15373/2249555X/APR2013/14.
P.C.S. Rani, L. R.K and G.S. Thara, Orient. J. Chem., 29, 315 (2013); https://doi.org/10.13005/ojc/290151.
G. Valarmathy and R. Subbalakshmi, Int. J. Pharm. Pharm. Sci., 5, 368 (2013).
W.J. Geary, Coord. Chem. Rev., 7, 81 (1971); https://doi.org/10.1016/S0010-8545(00)80009-0.
L.N. Sharda and M.C. Ganokar, Indian J. Chem., 27A, 617 (1988).
P. Chattopadhyay and C. Sinha, Indian J. Chem., 34A, 76 (1995).
T.R. Rao, S. Shrestha, A. Prasad and K.K. Narang, Synth. React. Inorg. Met.-Org. Chem., 32, 419 (2002); https://doi.org/10.1081/SIM-120003216.
R.C. Maurya and P. Patel, Spec. Lett., 32, 213 (1999); https://doi.org/10.1080/00387019909349979.
P.P. Bhargava, R. Bembi and M. Tyagi, J. Indian Chem. Soc., 60, 214 (1983).
R.C. Maurya, D.D. Mishra, S. Mukherjee and J. Dubey, Polyhedron, 14, 1351 (1995); https://doi.org/10.1016/0277-5387(94)00394-T.
J.D. Lee, Concise Inorganic Chemistry, Blackwell Science Publishers, edn 5, p. 967, (1999).
H.R. Singh and B.V. Agarwala, J. Indian Chem. Soc., 65, 591 (1988).
B.V. Agarwala, S. Hingorani, V. Puri, C.L. Khetrapal and G.A. Nagangowda, Transition Met. Chem., 19, 25 (1994); https://doi.org/10.1007/BF00166260.
D.J. Pasto, Organic Structure Determination, Prentice Hall, International, London (1969).
Z.H. Chohan and M.M. Naseer, Appl. Organomet. Chem., 21, 728 (2007); https://doi.org/10.1002/aoc.1279.
G.A. Mabbot, J. Chem. Educ., 60, 697 (1983); https://doi.org/10.1021/ed060p697.
Indian Pharmacopoeia, IIA, 105 (1996).
R. Cruickshank, J.O. Dugid, B.P. Marnion and R.H. Swain, Medical Microbiology, Churchill Livingston Publication, New York, edn 12, vol. II, p. 98 (1975).
T. Mosmann, J. Immunol. Methods, 65, 55 (1983); https://doi.org/10.1016/0022-1759(83)90303-4.
M. Navarra, M. Celano, J. Maiuolo, S. Schenone, M. Botta, A. Angelucci, P. Bramanti and D. Russo, BMC Cancer, 10, 602 (2010); https://doi.org/10.1186/1471-2407-10-602.
H.R. Park, C.H. Oh, H.C. Lee, J.G. Choi, B.I. Jung and K.M. Bark, Bull. Korean Chem. Soc., 27, 2002 (2006); https://doi.org/10.5012/bkcs.2006.27.12.2002.
S. Jagadeeswari, M.A. Jhonsi, A. Kathiravan and R. Renganathan, J. Lumin., 131, 597 (2011); https://doi.org/10.1016/j.jlumin.2010.10.037.