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Synthesis, Characterization and Antimicrobial Activities of 1,2,4-Triazole-Coumarin Schiff Bases and their Mn(II), Co(II) Complexes
Corresponding Author(s) : G.S. Kalwania
Asian Journal of Chemistry,
Vol. 27 No. 11 (2015): Vol 27 Issue 11
Abstract
Manganese(II) and cobalt(II) metal complexes have been synthesized with newly synthesized Schiff bases derived from 8-formyl-7-hydroxy-4-methylcoumarin and 3-substituted 4-amino-5-mercapto- 1,2,4-triazole by microwave irradiation method as well as conventional method. Reaction achieved by microwave irradiation technique, require drastically reduced reaction time and provide high yield with improved selectivity as compared to conventional method. The synthesized compounds were characterized by elemental analysis, spectral studies, magnetic measurements and thermal studies. The elemental analysis were clearly indicated that ML·2H2O type complexes have 1:1 stoichiometry (M = metal, L = ligand). All the Mn(II) and Co(II) complexes were stable at room temperature, non-hygroscopic, insoluble in water and all of them were polymeric in nature. The synthesized Schiff bases and their metal complexes screened for antimicrobial activities against selected bacteria and fungi.
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- C. Legrand, P. Ropa, B. Vulturescu, A.M. Hogea, G.G. Surpateanu, F. Cazier, P. Woisel and G. Surpateanu, Prog. Org. Coat., 53, 106 (2005); doi:10.1016/j.porgcoat.2004.11.011.
- N.F. Eweiss, A.A. Bahajaj and E.A. Elsherbini, J. Heterocycl. Chem., 23, 1451 (1986); doi:10.1002/jhet.5570230540.
- N.F. Eweiss and A.A. Bahajaj, J. Heterocycl. Chem., 24, 1173 (1987); doi:10.1002/jhet.5570240448.
- A. Prasad, R.J. Ramalingam, A.B. Rao, P.V. Diwan and P.B. Sattur, Eur. J. Med. Chem., 24, 199 (1989); doi:10.1016/0223-5234(89)90116-5.
- G. Turan-Zitouni, Z.A. Kaplancikli, M.T. Yildiz, P. Chevallet and D. Kaya, Eur. J. Med. Chem., 40, 607 (2005); doi:10.1016/j.ejmech.2005.01.007.
- J. Chen, X.Y. Sun, K.Y. Chai, J.S. Lee, M.S. Song and Z.S. Quan, Bioorg. Med. Chem., 15, 6775 (2007); doi:10.1016/j.bmc.2007.08.004.
- O. Bekircan and N. Gumrukcuoglu, Indian J. Chem., 44B, 2107 (2005).
- G. Turan-Zitouni, Z.A. Kaplancikli, K. Erol and F.S. Kilic, Farmaco, 54, 218 (1999); doi:10.1016/S0014-827X(99)00016-6.
- T. Akhtar, S. Hameed, N.A. Al-Masoudi and K.M. Khan, Heteroatom Chem., 18, 316 (2007); doi:10.1002/hc.20282.
- G. Turan-Zitouni, Z.A. Kaplancikli, A. Özdemir, P. Chevallet, H.B. Kandilci and B. Gümüsel, Arch. Pharm. Chem. Life Sci., 340, 586 (2007); doi:10.1002/ardp.200700134.
- L. Pochet, C. Doucet, M. Schynts, N. Thierry, N. Boggetto, B. Pirotte, K.Y. Jiang, B. Masereel, P. de Tullio, J. Delarge and M. Reboud-Ravaux, J. Med. Chem., 39, 2579 (1996); doi:10.1021/jm960090b.
- X. Shao, D.H.L. Ekstrand, R. Bhikhabhai, C.F.R. Kallander and J.S. Gronowitz, Antivir. Chem. Chemother., 8, 149 (1997); doi:10.1177/095632029700800209.
- B. Rendenbach-Müller, R. Schlecker, M. Traut and H. Weifenbach, Bioorg. Med. Chem. Lett., 4, 1195 (1994); doi:10.1016/S0960-894X(01)80328-0.
- I. Kostova, G. Momekov, T. Tzanova and M. Karaivanova, Bioinorg. Chem. Appl., Article ID 25651 (2006); doi:10.1155/BCA/2006/25651.
- I. Kostova, Curr. Med. Chem. Anticancer Agents, 5, 29 (2005); doi:10.2174/1568011053352550.
- U.S. Weber, B. Steffen and C. Sigers, Res. Commun. Mol. Pathol. Pharmacol., 99, 193 (1998).
- I. Kostova, I. Manolov and M. Karaivanova, Arch. Pharm., 334, 157 (2001); doi:10.1002/1521-4184(200105)334:5<157::AID-ARDP157>3.0.CO;2-S.
- G.B. Bagihalli, P.G. Avaji, S.A. Patil and P.S. Badami, Eur. J. Med. Chem., 43, 2639 (2008); doi:10.1016/j.ejmech.2008.02.013.
- S. Caddick, Tetrahedron, 51, 10403 (1995); doi:10.1016/0040-4020(95)00662-R.
- M. Kidwai, P. Sapra, K.R. Bhushan, R.K. Saxena, R. Gupta and M. Singh, Monatsh. Chem., 113, 85 (2000); doi:10.1007/PL00010299.
- C.O. Kappe, Curr. Opin. Chem. Biol., 6, 314 (2002); doi:10.1016/S1367-5931(02)00306-X.
- M. Larhed, C. Moberg and A. Hallberg, Acc. Chem. Res., 35, 717 (2002); doi:10.1021/ar010074v.
- P. Lidström, J. Tierney, B. Wathey and J. Westman, Tetrahedron, 57, 9225 (2001); doi:10.1016/S0040-4020(01)00906-1.
- G.S. Kalwania, S. Choudhary and S. Chomal, Chem. Sci. Trans., 3, 1147 (2014); doi:10.7598/cst2014.847.
- V. Mathew, J. Keshavayya and V.P. Vaidya, J. Chem., 4, 320 (2007).
- K. Sanjeev S. Lamani, O. Kotresh, M.S.A. Phaniband and J.C. Kadakol, E-J.Chem., 6(S1), S239 (2009); doi:10.1155/2009/787150.
- G. Singh, P.A. Singh, K. Singh, D.P. Singh, R.N. Handa and S.N. Dubey, Proc. Natl. Acad. Sci. Ind., 72A, 87 (2002).
- W.J. Geary, Coord. Chem. Rev., 7, 81 (1971); doi:10.1016/S0010-8545(00)80009-0.
- V.J. Tyagi, R.V. Ranbaore, V. Atre and M.C. Ganorkar, J. Indian Chem. Soc., 59, 199 (1982).
- F.D. Lewis and S.V. Barancyk, J. Am. Chem. Soc., 111, 8653 (1989); doi:10.1021/ja00205a015.
- P.R. Shukla, V.K. Singh, A.M. Jaiswal and J. Narain, J. Indian Chem. Soc., 60, 321 (1983).
- T. Kaliyappan, S. Rajagopan and P. Kannan, J. Appl. Polym. Sci., 91, 494 (2004); doi:10.1002/app.13138.
- G.S.V. Kumar and B. Mathew, J. Mac. Sci., 41, 1037 (2004).
- B.S. Creaven, D.A. Egan, K. Kavanagh, M. McCann, A. Noble, B. Thati and M. Walsh, Inorg. Chim. Acta, 359, 3976 (2006); doi:10.1016/j.ica.2006.04.006.
- M.S. Gunthkal, T.R. Goudar and S.A. Patil, J. Orient. Chem., 16, 151 (2000).
- S. Rao, Asian J. Chem., 17, 2663 (2005).
- S.A. Patil, B.M. Badiger, S.M. Kudari and V.H. Kulkarni, Transition Metal Chem., 8, 238 (1983); doi:10.1007/BF00620701.
- A.B.P. Lever, Inorganic Electronic Spectroscopy, Elsevier, Amsterdam (1984).
- S.M.E. Khalil, Chem. Pap., 54, 12 (2000).
- C.J. Balhausen, Introduction to Ligand Fields, McGraw Hill, New York (1962).
References
C. Legrand, P. Ropa, B. Vulturescu, A.M. Hogea, G.G. Surpateanu, F. Cazier, P. Woisel and G. Surpateanu, Prog. Org. Coat., 53, 106 (2005); doi:10.1016/j.porgcoat.2004.11.011.
N.F. Eweiss, A.A. Bahajaj and E.A. Elsherbini, J. Heterocycl. Chem., 23, 1451 (1986); doi:10.1002/jhet.5570230540.
N.F. Eweiss and A.A. Bahajaj, J. Heterocycl. Chem., 24, 1173 (1987); doi:10.1002/jhet.5570240448.
A. Prasad, R.J. Ramalingam, A.B. Rao, P.V. Diwan and P.B. Sattur, Eur. J. Med. Chem., 24, 199 (1989); doi:10.1016/0223-5234(89)90116-5.
G. Turan-Zitouni, Z.A. Kaplancikli, M.T. Yildiz, P. Chevallet and D. Kaya, Eur. J. Med. Chem., 40, 607 (2005); doi:10.1016/j.ejmech.2005.01.007.
J. Chen, X.Y. Sun, K.Y. Chai, J.S. Lee, M.S. Song and Z.S. Quan, Bioorg. Med. Chem., 15, 6775 (2007); doi:10.1016/j.bmc.2007.08.004.
O. Bekircan and N. Gumrukcuoglu, Indian J. Chem., 44B, 2107 (2005).
G. Turan-Zitouni, Z.A. Kaplancikli, K. Erol and F.S. Kilic, Farmaco, 54, 218 (1999); doi:10.1016/S0014-827X(99)00016-6.
T. Akhtar, S. Hameed, N.A. Al-Masoudi and K.M. Khan, Heteroatom Chem., 18, 316 (2007); doi:10.1002/hc.20282.
G. Turan-Zitouni, Z.A. Kaplancikli, A. Özdemir, P. Chevallet, H.B. Kandilci and B. Gümüsel, Arch. Pharm. Chem. Life Sci., 340, 586 (2007); doi:10.1002/ardp.200700134.
L. Pochet, C. Doucet, M. Schynts, N. Thierry, N. Boggetto, B. Pirotte, K.Y. Jiang, B. Masereel, P. de Tullio, J. Delarge and M. Reboud-Ravaux, J. Med. Chem., 39, 2579 (1996); doi:10.1021/jm960090b.
X. Shao, D.H.L. Ekstrand, R. Bhikhabhai, C.F.R. Kallander and J.S. Gronowitz, Antivir. Chem. Chemother., 8, 149 (1997); doi:10.1177/095632029700800209.
B. Rendenbach-Müller, R. Schlecker, M. Traut and H. Weifenbach, Bioorg. Med. Chem. Lett., 4, 1195 (1994); doi:10.1016/S0960-894X(01)80328-0.
I. Kostova, G. Momekov, T. Tzanova and M. Karaivanova, Bioinorg. Chem. Appl., Article ID 25651 (2006); doi:10.1155/BCA/2006/25651.
I. Kostova, Curr. Med. Chem. Anticancer Agents, 5, 29 (2005); doi:10.2174/1568011053352550.
U.S. Weber, B. Steffen and C. Sigers, Res. Commun. Mol. Pathol. Pharmacol., 99, 193 (1998).
I. Kostova, I. Manolov and M. Karaivanova, Arch. Pharm., 334, 157 (2001); doi:10.1002/1521-4184(200105)334:5<157::AID-ARDP157>3.0.CO;2-S.
G.B. Bagihalli, P.G. Avaji, S.A. Patil and P.S. Badami, Eur. J. Med. Chem., 43, 2639 (2008); doi:10.1016/j.ejmech.2008.02.013.
S. Caddick, Tetrahedron, 51, 10403 (1995); doi:10.1016/0040-4020(95)00662-R.
M. Kidwai, P. Sapra, K.R. Bhushan, R.K. Saxena, R. Gupta and M. Singh, Monatsh. Chem., 113, 85 (2000); doi:10.1007/PL00010299.
C.O. Kappe, Curr. Opin. Chem. Biol., 6, 314 (2002); doi:10.1016/S1367-5931(02)00306-X.
M. Larhed, C. Moberg and A. Hallberg, Acc. Chem. Res., 35, 717 (2002); doi:10.1021/ar010074v.
P. Lidström, J. Tierney, B. Wathey and J. Westman, Tetrahedron, 57, 9225 (2001); doi:10.1016/S0040-4020(01)00906-1.
G.S. Kalwania, S. Choudhary and S. Chomal, Chem. Sci. Trans., 3, 1147 (2014); doi:10.7598/cst2014.847.
V. Mathew, J. Keshavayya and V.P. Vaidya, J. Chem., 4, 320 (2007).
K. Sanjeev S. Lamani, O. Kotresh, M.S.A. Phaniband and J.C. Kadakol, E-J.Chem., 6(S1), S239 (2009); doi:10.1155/2009/787150.
G. Singh, P.A. Singh, K. Singh, D.P. Singh, R.N. Handa and S.N. Dubey, Proc. Natl. Acad. Sci. Ind., 72A, 87 (2002).
W.J. Geary, Coord. Chem. Rev., 7, 81 (1971); doi:10.1016/S0010-8545(00)80009-0.
V.J. Tyagi, R.V. Ranbaore, V. Atre and M.C. Ganorkar, J. Indian Chem. Soc., 59, 199 (1982).
F.D. Lewis and S.V. Barancyk, J. Am. Chem. Soc., 111, 8653 (1989); doi:10.1021/ja00205a015.
P.R. Shukla, V.K. Singh, A.M. Jaiswal and J. Narain, J. Indian Chem. Soc., 60, 321 (1983).
T. Kaliyappan, S. Rajagopan and P. Kannan, J. Appl. Polym. Sci., 91, 494 (2004); doi:10.1002/app.13138.
G.S.V. Kumar and B. Mathew, J. Mac. Sci., 41, 1037 (2004).
B.S. Creaven, D.A. Egan, K. Kavanagh, M. McCann, A. Noble, B. Thati and M. Walsh, Inorg. Chim. Acta, 359, 3976 (2006); doi:10.1016/j.ica.2006.04.006.
M.S. Gunthkal, T.R. Goudar and S.A. Patil, J. Orient. Chem., 16, 151 (2000).
S. Rao, Asian J. Chem., 17, 2663 (2005).
S.A. Patil, B.M. Badiger, S.M. Kudari and V.H. Kulkarni, Transition Metal Chem., 8, 238 (1983); doi:10.1007/BF00620701.
A.B.P. Lever, Inorganic Electronic Spectroscopy, Elsevier, Amsterdam (1984).
S.M.E. Khalil, Chem. Pap., 54, 12 (2000).
C.J. Balhausen, Introduction to Ligand Fields, McGraw Hill, New York (1962).