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Synthesis, Stereochemical and Biological Studies of Mono-nitrophenol Complexes with Benzofurathiosemicarbazide Ligand
Asian Journal of Chemistry,
Vol. 30 No. 8 (2018): Vol 30 Issue 8
Abstract
The present work deals with the preparation and characterization of complexes of benzofuron-2-carboxyphenyl thiosemicarbazide and benzofuro-2-carboxy-[4'-chlorophenyl]thiosemicarbazide with Co(II), Ni(II), Mn(II), Cu(II) and Zn(II) mono-nitrophenates. The structure of newly synthesized metal complexes and the ligands were established with UV-visible spectroscopy, infrared spectroscopy and magnetic studies. The ligand and the metal complexes were also screened and evaluated for their fungicidal activity against different fungi using growth method.
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- G. Domagk, Am. Rev. Tubercul. Pulmon. Dis., 61, 8 (1950).
- S. Sardari, S. Feizi, A.H. Rezayan, P. Azerang, S.M. Shahcheragh, G. Ghavami and A. Habibi, Iran. J. Pharm. Res., 16, 1128 (2017).
- Z.A. Kaplancikli, M.D. Altintop, B. Sever, Z. Cantürk and A. Özdemir, J. Chem., Article ID 1692540, (2016) https://doi.org/10.1155/2016/1692540.
- D.M. Wiles, B.A. Gingras and T. Suprunchuk, Can. J. Chem., 45, 1735 (1967); https://doi.org/10.1139/v67-282.
- Y. Yu, D.S. Kalinowski, Z. Kovacevic, A.R. Siafakas, P.J. Jansson, C. Stefani, D.B. Lovejoy, P.C. Sharpe, P.V. Bernhardt and D.R. Richardson, J. Med. Chem., 52, 5271 (2009); https://doi.org/10.1021/jm900552r.
- T. Khan, R. Ahmad, S. Joshi and A.R. Khan, Der Chem. Sinica, 6, 1 (2015).
- S. Padhye, Z. Afrasiabi, E. Sinn, J. Fok, K. Mehta and N. Rath, Inorg. Chem., 44, 1154 (2005); https://doi.org/10.1021/ic048214v.
- I.H. Krakoff, E. Ercubanas, C. Tan, K. Mayer, V. Tethune and J.H. Brechenal, Cancer Chemother. Rep., 58, 207 (1974).
- F.A. French, E.J. Blanz, S.C. Shaddix and R.W. Brockman, Med. Chem. (N.Y.), 17, 172 (1974); https://doi.org/10.1021/jm00248a006.
- K.C. Agrawal, A.J. Lin, B.A. Booth, J.R. Wheaton and A.C. Sartorelli, J. Med. Chem., 17, 631 (1974); https://doi.org/10.1021/jm00252a012.
- D.J. Bauer, L.S. Vincent, C.H. Kempe and A.W. Downie, Lancet, 20, 494 (1964).
- J.A. Crim and H.G. Petering, Cancer Res., 27, 1278 (1967).
- J. Li, B.S.P. Li-mou Zheng, I. King, T. Doyle and S.-H. Chen, Curr. Med. Chem., 8, 121 (2001); https://doi.org/10.2174/0929867013373741.
- R. Rosell, M. Tarón and A. O’Brate, Curr. Opin. Oncol., 13, 101 (2001); https://doi.org/10.1097/00001622-200103000-00004.
- G. Pelosi, The Open Crystallogr. J., 3, 16 (2010); https://doi.org/10.2174/1874846501003010016.
- D.X. West, A.E. Liberta, S.B. Padhye, R.C. Chikate, P.B. Sonawane, A.S. Kumbhar and R.G. Yerande, Coord. Chem. Rev., 123, 49 (1993); https://doi.org/10.1016/0010-8545(93)85052-6.
- L.N. Suvarapu, A.R. Somala, J.R. Koduru, S.O. Baek and V.R. Ammireddy, Asian J. Chem., 24, 1889 (2012).
- S.L. Mostafa, A.A. El-Asmy and M.S. El-Shahawi, Transition Met. Chem., 25, 470 (2000); https://doi.org/10.1023/A:1007074415445.
- K.M. Ibrahim, Synth. React. Inorg. Met.-Org. Chem., 23, 1351 (1993); https://doi.org/10.1080/15533179308016691.
- S.L. Mostafa and M.M. Bekheit, Chem. Pharm. Bull. Japan, 48, 266 (2000); https://doi.org/10.1248/cpb.48.266.
- K.M. Ibrahim, S.I. Mostafa, N. Nawar and Z.A. Younis, Indian J. Chem., 43A, 2294 (2004).
- K.H. Reddy, Resonance, 4, 67 (1999); https://doi.org/10.1007/BF02834637.
- S.S. David and E. Meggers, Curr. Opin. Chem. Biol., 12, 194 (2008); https://doi.org/10.1016/j.cbpa.2008.03.008.
- H. Martin, R.L. Wain and E.H. Wilkinson, Appl. Biol., 29, 412 (1942); https://doi.org/10.1111/j.1744-7348.1942.tb06146.x.
- G.A. Carter and R.L. Wain, Ann. Appl. Biol., 53, 291 (1964); https://doi.org/10.1111/j.1744-7348.1964.tb03804.x.
- K. Kuraoka, Y. Chujo and T. Yazawa, Chem. Commun., 2477 (2000); https://doi.org/10.1039/B007925L.
- X.-Y. Wei, J.-Z. Li, Z.-H. Mao, B. Zhou and S.-Y. Qin, Chin. J. Chem., 22, 558 (2004); https://doi.org/10.1002/cjoc.20040220613.
- U. Ndagi, N. Mhlongo and M.E. Soliman, Drug Design, Develop. Ther., 11, 599 (2017); https://doi.org/10.2147/DDDT.S119488.
- K.L. Haas and K.J. Franz, Chem. Rev., 109, 4921 (2009); https://doi.org/10.1021/cr900134a.
- B.J. Pages, D.L. Ang, E.P. Wright and J.R. Aldrich-Wright, Dalton Trans., 44, 3505 (2015); https://doi.org/10.1039/C4DT02700K.
- B. Singh, R.N. Singh and R.C. Aggarwal, Polyhedron, 4, 401 (1985); https://doi.org/10.1016/S0277-5387(00)86999-5.
- K.M. Ibrahim, S.I. Mostafa, N.Y. Nawar and A. Zeinab, Indian J. Chem., 43A, 2294 (2004).
- R. Garg, M.K. Saini N. Fahmi and R.V. Singh, Indian J. Chem., 44A, 2433 (2005).
- M.B. Halli and Z.S. Qureshi, Indian J. Chem., 43A, 2347 (2004).
- A.A. El-Asmy and M.M. Mostafa, Polyhedron, 2, 591 (1983); https://doi.org/10.1016/S0277-5387(00)81516-8.
- D. Khanna, V. Banerjee, B.V. Agarwal and A.K. Dey, Indian J. Chem., 21A, 621 (1982).
- M.M. Mostafa, A.A. El-Asmy and G.M. Ibrahim, Transition Met. Chem., 8, 54 (1983); https://doi.org/10.1007/BF00618800.
- S. Rao and K.H. Reddy, Indian J. Chem., 35A, 681 (1996).
- N.K. Dutt and N.C. Chakder, J. Inorg. Nucl. Chem., 33, 393 (1971); https://doi.org/10.1016/0022-1902(71)80381-0.
- C.N.R. Rao and R. Venkataraghavan, Spectrochim. Acta, 18, 541 (1962); https://doi.org/10.1016/S0371-1951(62)80164-7.
- B.N. Figgis and J. Lewis, Techniques of Inorganic Chemistry, Wiley Interscience, New York, Wiley, p. 66 Chap. 3 (1965)
References
G. Domagk, Am. Rev. Tubercul. Pulmon. Dis., 61, 8 (1950).
S. Sardari, S. Feizi, A.H. Rezayan, P. Azerang, S.M. Shahcheragh, G. Ghavami and A. Habibi, Iran. J. Pharm. Res., 16, 1128 (2017).
Z.A. Kaplancikli, M.D. Altintop, B. Sever, Z. Cantürk and A. Özdemir, J. Chem., Article ID 1692540, (2016) https://doi.org/10.1155/2016/1692540.
D.M. Wiles, B.A. Gingras and T. Suprunchuk, Can. J. Chem., 45, 1735 (1967); https://doi.org/10.1139/v67-282.
Y. Yu, D.S. Kalinowski, Z. Kovacevic, A.R. Siafakas, P.J. Jansson, C. Stefani, D.B. Lovejoy, P.C. Sharpe, P.V. Bernhardt and D.R. Richardson, J. Med. Chem., 52, 5271 (2009); https://doi.org/10.1021/jm900552r.
T. Khan, R. Ahmad, S. Joshi and A.R. Khan, Der Chem. Sinica, 6, 1 (2015).
S. Padhye, Z. Afrasiabi, E. Sinn, J. Fok, K. Mehta and N. Rath, Inorg. Chem., 44, 1154 (2005); https://doi.org/10.1021/ic048214v.
I.H. Krakoff, E. Ercubanas, C. Tan, K. Mayer, V. Tethune and J.H. Brechenal, Cancer Chemother. Rep., 58, 207 (1974).
F.A. French, E.J. Blanz, S.C. Shaddix and R.W. Brockman, Med. Chem. (N.Y.), 17, 172 (1974); https://doi.org/10.1021/jm00248a006.
K.C. Agrawal, A.J. Lin, B.A. Booth, J.R. Wheaton and A.C. Sartorelli, J. Med. Chem., 17, 631 (1974); https://doi.org/10.1021/jm00252a012.
D.J. Bauer, L.S. Vincent, C.H. Kempe and A.W. Downie, Lancet, 20, 494 (1964).
J.A. Crim and H.G. Petering, Cancer Res., 27, 1278 (1967).
J. Li, B.S.P. Li-mou Zheng, I. King, T. Doyle and S.-H. Chen, Curr. Med. Chem., 8, 121 (2001); https://doi.org/10.2174/0929867013373741.
R. Rosell, M. Tarón and A. O’Brate, Curr. Opin. Oncol., 13, 101 (2001); https://doi.org/10.1097/00001622-200103000-00004.
G. Pelosi, The Open Crystallogr. J., 3, 16 (2010); https://doi.org/10.2174/1874846501003010016.
D.X. West, A.E. Liberta, S.B. Padhye, R.C. Chikate, P.B. Sonawane, A.S. Kumbhar and R.G. Yerande, Coord. Chem. Rev., 123, 49 (1993); https://doi.org/10.1016/0010-8545(93)85052-6.
L.N. Suvarapu, A.R. Somala, J.R. Koduru, S.O. Baek and V.R. Ammireddy, Asian J. Chem., 24, 1889 (2012).
S.L. Mostafa, A.A. El-Asmy and M.S. El-Shahawi, Transition Met. Chem., 25, 470 (2000); https://doi.org/10.1023/A:1007074415445.
K.M. Ibrahim, Synth. React. Inorg. Met.-Org. Chem., 23, 1351 (1993); https://doi.org/10.1080/15533179308016691.
S.L. Mostafa and M.M. Bekheit, Chem. Pharm. Bull. Japan, 48, 266 (2000); https://doi.org/10.1248/cpb.48.266.
K.M. Ibrahim, S.I. Mostafa, N. Nawar and Z.A. Younis, Indian J. Chem., 43A, 2294 (2004).
K.H. Reddy, Resonance, 4, 67 (1999); https://doi.org/10.1007/BF02834637.
S.S. David and E. Meggers, Curr. Opin. Chem. Biol., 12, 194 (2008); https://doi.org/10.1016/j.cbpa.2008.03.008.
H. Martin, R.L. Wain and E.H. Wilkinson, Appl. Biol., 29, 412 (1942); https://doi.org/10.1111/j.1744-7348.1942.tb06146.x.
G.A. Carter and R.L. Wain, Ann. Appl. Biol., 53, 291 (1964); https://doi.org/10.1111/j.1744-7348.1964.tb03804.x.
K. Kuraoka, Y. Chujo and T. Yazawa, Chem. Commun., 2477 (2000); https://doi.org/10.1039/B007925L.
X.-Y. Wei, J.-Z. Li, Z.-H. Mao, B. Zhou and S.-Y. Qin, Chin. J. Chem., 22, 558 (2004); https://doi.org/10.1002/cjoc.20040220613.
U. Ndagi, N. Mhlongo and M.E. Soliman, Drug Design, Develop. Ther., 11, 599 (2017); https://doi.org/10.2147/DDDT.S119488.
K.L. Haas and K.J. Franz, Chem. Rev., 109, 4921 (2009); https://doi.org/10.1021/cr900134a.
B.J. Pages, D.L. Ang, E.P. Wright and J.R. Aldrich-Wright, Dalton Trans., 44, 3505 (2015); https://doi.org/10.1039/C4DT02700K.
B. Singh, R.N. Singh and R.C. Aggarwal, Polyhedron, 4, 401 (1985); https://doi.org/10.1016/S0277-5387(00)86999-5.
K.M. Ibrahim, S.I. Mostafa, N.Y. Nawar and A. Zeinab, Indian J. Chem., 43A, 2294 (2004).
R. Garg, M.K. Saini N. Fahmi and R.V. Singh, Indian J. Chem., 44A, 2433 (2005).
M.B. Halli and Z.S. Qureshi, Indian J. Chem., 43A, 2347 (2004).
A.A. El-Asmy and M.M. Mostafa, Polyhedron, 2, 591 (1983); https://doi.org/10.1016/S0277-5387(00)81516-8.
D. Khanna, V. Banerjee, B.V. Agarwal and A.K. Dey, Indian J. Chem., 21A, 621 (1982).
M.M. Mostafa, A.A. El-Asmy and G.M. Ibrahim, Transition Met. Chem., 8, 54 (1983); https://doi.org/10.1007/BF00618800.
S. Rao and K.H. Reddy, Indian J. Chem., 35A, 681 (1996).
N.K. Dutt and N.C. Chakder, J. Inorg. Nucl. Chem., 33, 393 (1971); https://doi.org/10.1016/0022-1902(71)80381-0.
C.N.R. Rao and R. Venkataraghavan, Spectrochim. Acta, 18, 541 (1962); https://doi.org/10.1016/S0371-1951(62)80164-7.
B.N. Figgis and J. Lewis, Techniques of Inorganic Chemistry, Wiley Interscience, New York, Wiley, p. 66 Chap. 3 (1965)