Copyright (c) 2019 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis, Characterization and Biological Studies of Novel Schiff Base viz. Bis-1,1'-(pyridine-2,6-diyldieth-1-yl-1-ylidene) biguanidine and Their Transition Metal Complexes
Corresponding Author(s) : Manoj Kumar
Asian Journal of Chemistry,
Vol. 31 No. 4 (2019): Vol 31 Issue 4
Abstract
Novel Schiff base and its two transition metal complexes derived from the condensation reaction of 2,6-diacetylpyridine with biguanide, characterized by 1H NMR, IR and elemental analysis. The ligand and its cobalt(II) and nickel(II) complexes showed potent DNA photo-cleavage activity. Antimicrobial activity of this Schiff base and its cobalt(II) and nickel(II) complexes against bacteria and fungi viz. S. aureus, K. pneumoniaae and A. niger, Trichophyton rubrum, respectively was evaluated in terms of zone of inhibition.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- D D. Sinha, A.K. Tiwari, S. Singh, G. Shukla, P. Mishra, H. Chandra and A.K. Mishra, Eur. J. Med. Chem., 43, 160 (2008); https://doi.org/10.1016/j.ejmech.2007.03.022.
- A. Kajal, S. Bala, S. Kamboj, N. Sharma and V. Saini, J. Catalysts, 2013, Article ID 893512 (2013); https://doi.org/10.1155/2013/893512.
- M.N. Ibrahim and S.A.I. Sharif, E-J. Chem., 8, 180 (2011); https://doi.org/10.1155/2011/821616.
- M. Mustapha, B.R. Thorat, S. Sawant, R.G. Atram and R. Yamgar, J. Chem. Pharm. Res., 3, 5 (2011).
- N.M. Sabry, E.M. Flefel, M.A. Al-Omar and A.E.G.E. Amr, J. Chem., 2013, Article ID 106734 (2013); https://doi.org/10.1155/2013/106734.
- M. Akbar Ali, A.H. Mirza, C.W. Voo, A.L. Tan and P.V. Bernhardt, Polyhedron, 22, 3433 (2003); https://doi.org/10.1016/j.poly.2003.08.004.
- M.M.H. Khalil, E.H. Ismail, G.G. Mohamed, E.M. Zayed and A. Badr, Open J. Inorg. Chem., 2, 13 (2012); https://doi.org/10.4236/ojic.2012.22003.
- A. Mumtaz, T. Mahmud and E. Mr, J. Nucl. Med. Radiat. Ther., 7, 1 (2016); https://doi.org/10.4172/2155-9619.1000310.
- M.S. Hossain and C.M. Zakaria, Der Chemica Sinica, 8, 380 (2017).
- A. Rani, M. Kumar, R. Khare and H.S. Tuli, J. Biol. Chem. Sci., 2, 62 (2015).
- H.R. Bridges, A.J.Y. Jones, M.N. Pollak and J. Hirst, Biochem. J., 462, 475 (2014); https://doi.org/10.1042/BJ20140620.
- R. Olar, M. Badea, D. Marinescu, M.-C. Chifiriuc, C. Bleotu, M.N. Grecu, E.-E. Iorgulescu and V. Lazar, Eur. J. Med. Chem., 45, 3027 (2010); https://doi.org/10.1016/j.ejmech.2010.03.033.
- P. Broxton, P.M. Woodcock and P. Gilbert, J. Appl. Bacteriol., 54, 345 (1983); https://doi.org/10.1111/j.1365-2672.1983.tb02627.x.
- M. Asif, J. Educ. Health Promot., 3, 1 (2014); https://doi.org/10.4103/2277-9531.127541.
- S.M. Abu-El-Wafa, M.A. El-Ries and F.H. Ahmed, Inorg. Chim. Acta, 136, 127 (1987); https://doi.org/10.1016/S0020-1693(00)81143-3.
- T. Ikeda, S. Tazuke and M. Watanabe, Biochim. Biophys. Acta, 735, 380 (1983); https://doi.org/10.1016/0005-2736(83)90152-9.
- P. Vasantha, B.S. Kumar, B. Shekhar and P.V.A. Lakshmi, Appl. Organomet. Chem., 32, e4254 (2018); https://doi.org/10.1002/aoc.4254.
- K.B. Gudasi, S.A. Patil, R.S. Vadavi, R.V. Shenoy and M.S. Pati, Transition Met. Chem., 30, 1014 (2005); https://doi.org/10.1007/s11243-005-6297-z.
- H. Köksal, M. Dolaz, M. Tümer and S. Serin, Synth. React. Inorg. Met.-Org. Chem., 31, 1141 (2001); https://doi.org/10.1081/SIM-100106854.
- P. Dhanakodi, M. Jayandran and V. Balasubramanian, J. Mater. Sci. Elect., 29, 7526 (2018); https://doi.org/10.1007/s10854-018-8744-6.
- M. Kumar and G.R. Verma, Orient. J. Chem., 26, 517 (2010).
- R. Gup, C. Gökçe and N. Dilek, Supramol. Chem., 27, 629 (2015); https://doi.org/10.1080/10610278.2015.1051978.
- M. Tyagi and S. Chandra, Open J. Inorg. Chem., 2, 41 (2012); https://doi.org/10.4236/ojic.2012.23007.
- A.A.A. Abou-Hussen and W. Linert, Synth. React. Inorg. Met.-Org. Nano-Met. Chem., 39, 570 (2009); https://doi.org/10.1080/15533170903327950.
- M.C. Rodriguez-Argüelles, M.B. Ferrari, G.G. Fava, C. Pelizzi, P. Tarasconi, R. Albertini, P.P. Dall’Aglio, P. Lunghi and S. Pinelli, J. Inorg. Biochem., 58, 157 (1995); https://doi.org/10.1016/0162-0134(94)00043-A.
- M. Roy, B. Pathak, A.K. Patra, E.D. Jemmis, M. Nethaji and A.R. Chakravarty, Inorg. Chem., 46, 11122 (2007); https://doi.org/10.1021/ic701450a.
- S.N. Holter and W.C. Fernelius, Inorg. Synt., 7, 56 (1963).
- T.N.L. Pfoze, Y. Kumar, B. Myrboh, R.K. Bhagobaty and S.R. Joshi, J. Med. Plan Res., 5, 859 (2009).
- E.A. ter Laak, J.H. Noordergraaf and M.H. Verschure, Antimicrob. Agents Chemother., 37, 317 (1993); https://doi.org/10.1128/AAC.37.2.317.
- L.J. Althaher, Rafidain J. Sci., 24, 25 (2013).
- R. Pal, V. Kumar, A.K. Gupta and V. Beniwal, Med. Chem. Res., 23, 3327 (2014); https://doi.org/10.1007/s00044-014-0911-6.
- M. Mohan, P. Sharma, M. Kumar and N.K. Jha, Inorg. Chim. Acta, 9, 125 (1986).
- L.C.Y. Woo, V.G. Yuen, K.H. Thompson, J.H. McNeill and C. Orvig, J. Inorg. Biochem., 76, 251 (1999); https://doi.org/10.1016/S0162-0134(99)00152-X.
- J.S. Flier, L.H. Underhill and G.S. Eisenbarth, N. Engl. J. Med., 314, 1360 (1986); https://doi.org/10.1056/NEJM198605223142106.
- R.A. DeFronzo, R.C. Bonadonna and E. Ferrannini, Diabetes Care, 15, 318 (1992); https://doi.org/10.2337/diacare.15.3.318.
- H. Naeimi, H. Sharghi, F. Salimi and K. Rabiei, Heteroatom. Chem., 19, 43 (2008); https://doi.org/10.1002/hc.20383.
- R. Kaushal and S. Thakur, Chem. Eng. Trans., 32, 1801 (2013); https://doi.org/10.3303/CET1332301.
- S.K. Bharti, G. Nath, R. Tilak and S.K. Singh, Eur. J. Med. Chem., 45, 651 (2010); https://doi.org/10.1016/j.ejmech.2009.11.008.
- H. Naeimi, F. Salimi and K. Rabiei, J. Mol. Catal. Chem., 260, 100 (2006); https://doi.org/10.1016/j.molcata.2006.06.055.
- A.K. Singh, V.K. Gupta and B. Gupta, Anal. Chim. Acta, 585, 171 (2007); https://doi.org/10.1016/j.aca.2006.11.074.
- S. Rakshit, D. Palit, S.K.S. Hazari, S. Rabi, T.G. Roy, F. Olbrich and D. Rehder, Polyhedron, 117, 224 (2016); https://doi.org/10.1016/j.poly.2016.05.053.
- S. Chandra and M. Tyagi, J. Serb. Chem. Soc., 73, 727 (2008); https://doi.org/10.2298/JSC0807727C.
- M. Carcelli, P. Mazza, C. Pelizzi and F. Zani, J. lnorg. Biochem., 57, 43 (1995); https://doi.org/10.1016/0162-0134(94)00004-T.
- R. Olar, M. Badea, E. Cristurean, V. Lazar, R. Cernat and C. Balotescu, J. Therm. Anal. Calorim., 80, 451 (2005); https://doi.org/10.1007/s10973-005-0676-8.
- T.-F. Miao, J. Li, S. Li and N.-L. Wang, J. Phys. Chem. A, 118, 5692 (2014); https://doi.org/10.1021/jp502937b.
- J.L. García-Giménez, J. Hernández-Gil, A. Martínez-Ruíz, A. Castiñeiras, M. Liu-González, F.V. Pallardó, J. Borrás and G.A. Piña, J. Inorg. Biochem., 121, 167 (2013); https://doi.org/10.1016/j.jinorgbio.2013.01.003.
- T. Da Ros, G. Spalluto, A.S. Boutorine, R.V. Bensasson and M. Prato, Curr. Pharm. Des., 7, 1781 (2001); https://doi.org/10.2174/1381612013397140.
- P. Vasantha, B. Sathish Kumar, B. Shekhar and P.V. Anantha Lakshmi, Mater. Sci. Eng.: C, 90, 621 (2018); https://doi.org/10.1016/j.msec.2018.04.052.
References
D D. Sinha, A.K. Tiwari, S. Singh, G. Shukla, P. Mishra, H. Chandra and A.K. Mishra, Eur. J. Med. Chem., 43, 160 (2008); https://doi.org/10.1016/j.ejmech.2007.03.022.
A. Kajal, S. Bala, S. Kamboj, N. Sharma and V. Saini, J. Catalysts, 2013, Article ID 893512 (2013); https://doi.org/10.1155/2013/893512.
M.N. Ibrahim and S.A.I. Sharif, E-J. Chem., 8, 180 (2011); https://doi.org/10.1155/2011/821616.
M. Mustapha, B.R. Thorat, S. Sawant, R.G. Atram and R. Yamgar, J. Chem. Pharm. Res., 3, 5 (2011).
N.M. Sabry, E.M. Flefel, M.A. Al-Omar and A.E.G.E. Amr, J. Chem., 2013, Article ID 106734 (2013); https://doi.org/10.1155/2013/106734.
M. Akbar Ali, A.H. Mirza, C.W. Voo, A.L. Tan and P.V. Bernhardt, Polyhedron, 22, 3433 (2003); https://doi.org/10.1016/j.poly.2003.08.004.
M.M.H. Khalil, E.H. Ismail, G.G. Mohamed, E.M. Zayed and A. Badr, Open J. Inorg. Chem., 2, 13 (2012); https://doi.org/10.4236/ojic.2012.22003.
A. Mumtaz, T. Mahmud and E. Mr, J. Nucl. Med. Radiat. Ther., 7, 1 (2016); https://doi.org/10.4172/2155-9619.1000310.
M.S. Hossain and C.M. Zakaria, Der Chemica Sinica, 8, 380 (2017).
A. Rani, M. Kumar, R. Khare and H.S. Tuli, J. Biol. Chem. Sci., 2, 62 (2015).
H.R. Bridges, A.J.Y. Jones, M.N. Pollak and J. Hirst, Biochem. J., 462, 475 (2014); https://doi.org/10.1042/BJ20140620.
R. Olar, M. Badea, D. Marinescu, M.-C. Chifiriuc, C. Bleotu, M.N. Grecu, E.-E. Iorgulescu and V. Lazar, Eur. J. Med. Chem., 45, 3027 (2010); https://doi.org/10.1016/j.ejmech.2010.03.033.
P. Broxton, P.M. Woodcock and P. Gilbert, J. Appl. Bacteriol., 54, 345 (1983); https://doi.org/10.1111/j.1365-2672.1983.tb02627.x.
M. Asif, J. Educ. Health Promot., 3, 1 (2014); https://doi.org/10.4103/2277-9531.127541.
S.M. Abu-El-Wafa, M.A. El-Ries and F.H. Ahmed, Inorg. Chim. Acta, 136, 127 (1987); https://doi.org/10.1016/S0020-1693(00)81143-3.
T. Ikeda, S. Tazuke and M. Watanabe, Biochim. Biophys. Acta, 735, 380 (1983); https://doi.org/10.1016/0005-2736(83)90152-9.
P. Vasantha, B.S. Kumar, B. Shekhar and P.V.A. Lakshmi, Appl. Organomet. Chem., 32, e4254 (2018); https://doi.org/10.1002/aoc.4254.
K.B. Gudasi, S.A. Patil, R.S. Vadavi, R.V. Shenoy and M.S. Pati, Transition Met. Chem., 30, 1014 (2005); https://doi.org/10.1007/s11243-005-6297-z.
H. Köksal, M. Dolaz, M. Tümer and S. Serin, Synth. React. Inorg. Met.-Org. Chem., 31, 1141 (2001); https://doi.org/10.1081/SIM-100106854.
P. Dhanakodi, M. Jayandran and V. Balasubramanian, J. Mater. Sci. Elect., 29, 7526 (2018); https://doi.org/10.1007/s10854-018-8744-6.
M. Kumar and G.R. Verma, Orient. J. Chem., 26, 517 (2010).
R. Gup, C. Gökçe and N. Dilek, Supramol. Chem., 27, 629 (2015); https://doi.org/10.1080/10610278.2015.1051978.
M. Tyagi and S. Chandra, Open J. Inorg. Chem., 2, 41 (2012); https://doi.org/10.4236/ojic.2012.23007.
A.A.A. Abou-Hussen and W. Linert, Synth. React. Inorg. Met.-Org. Nano-Met. Chem., 39, 570 (2009); https://doi.org/10.1080/15533170903327950.
M.C. Rodriguez-Argüelles, M.B. Ferrari, G.G. Fava, C. Pelizzi, P. Tarasconi, R. Albertini, P.P. Dall’Aglio, P. Lunghi and S. Pinelli, J. Inorg. Biochem., 58, 157 (1995); https://doi.org/10.1016/0162-0134(94)00043-A.
M. Roy, B. Pathak, A.K. Patra, E.D. Jemmis, M. Nethaji and A.R. Chakravarty, Inorg. Chem., 46, 11122 (2007); https://doi.org/10.1021/ic701450a.
S.N. Holter and W.C. Fernelius, Inorg. Synt., 7, 56 (1963).
T.N.L. Pfoze, Y. Kumar, B. Myrboh, R.K. Bhagobaty and S.R. Joshi, J. Med. Plan Res., 5, 859 (2009).
E.A. ter Laak, J.H. Noordergraaf and M.H. Verschure, Antimicrob. Agents Chemother., 37, 317 (1993); https://doi.org/10.1128/AAC.37.2.317.
L.J. Althaher, Rafidain J. Sci., 24, 25 (2013).
R. Pal, V. Kumar, A.K. Gupta and V. Beniwal, Med. Chem. Res., 23, 3327 (2014); https://doi.org/10.1007/s00044-014-0911-6.
M. Mohan, P. Sharma, M. Kumar and N.K. Jha, Inorg. Chim. Acta, 9, 125 (1986).
L.C.Y. Woo, V.G. Yuen, K.H. Thompson, J.H. McNeill and C. Orvig, J. Inorg. Biochem., 76, 251 (1999); https://doi.org/10.1016/S0162-0134(99)00152-X.
J.S. Flier, L.H. Underhill and G.S. Eisenbarth, N. Engl. J. Med., 314, 1360 (1986); https://doi.org/10.1056/NEJM198605223142106.
R.A. DeFronzo, R.C. Bonadonna and E. Ferrannini, Diabetes Care, 15, 318 (1992); https://doi.org/10.2337/diacare.15.3.318.
H. Naeimi, H. Sharghi, F. Salimi and K. Rabiei, Heteroatom. Chem., 19, 43 (2008); https://doi.org/10.1002/hc.20383.
R. Kaushal and S. Thakur, Chem. Eng. Trans., 32, 1801 (2013); https://doi.org/10.3303/CET1332301.
S.K. Bharti, G. Nath, R. Tilak and S.K. Singh, Eur. J. Med. Chem., 45, 651 (2010); https://doi.org/10.1016/j.ejmech.2009.11.008.
H. Naeimi, F. Salimi and K. Rabiei, J. Mol. Catal. Chem., 260, 100 (2006); https://doi.org/10.1016/j.molcata.2006.06.055.
A.K. Singh, V.K. Gupta and B. Gupta, Anal. Chim. Acta, 585, 171 (2007); https://doi.org/10.1016/j.aca.2006.11.074.
S. Rakshit, D. Palit, S.K.S. Hazari, S. Rabi, T.G. Roy, F. Olbrich and D. Rehder, Polyhedron, 117, 224 (2016); https://doi.org/10.1016/j.poly.2016.05.053.
S. Chandra and M. Tyagi, J. Serb. Chem. Soc., 73, 727 (2008); https://doi.org/10.2298/JSC0807727C.
M. Carcelli, P. Mazza, C. Pelizzi and F. Zani, J. lnorg. Biochem., 57, 43 (1995); https://doi.org/10.1016/0162-0134(94)00004-T.
R. Olar, M. Badea, E. Cristurean, V. Lazar, R. Cernat and C. Balotescu, J. Therm. Anal. Calorim., 80, 451 (2005); https://doi.org/10.1007/s10973-005-0676-8.
T.-F. Miao, J. Li, S. Li and N.-L. Wang, J. Phys. Chem. A, 118, 5692 (2014); https://doi.org/10.1021/jp502937b.
J.L. García-Giménez, J. Hernández-Gil, A. Martínez-Ruíz, A. Castiñeiras, M. Liu-González, F.V. Pallardó, J. Borrás and G.A. Piña, J. Inorg. Biochem., 121, 167 (2013); https://doi.org/10.1016/j.jinorgbio.2013.01.003.
T. Da Ros, G. Spalluto, A.S. Boutorine, R.V. Bensasson and M. Prato, Curr. Pharm. Des., 7, 1781 (2001); https://doi.org/10.2174/1381612013397140.
P. Vasantha, B. Sathish Kumar, B. Shekhar and P.V. Anantha Lakshmi, Mater. Sci. Eng.: C, 90, 621 (2018); https://doi.org/10.1016/j.msec.2018.04.052.