Copyright (c) 2018 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis, Characterization and Biological Activities of Mercury(II) Ternary Complexes of 2-Substituted Benzothiazoles Derivatives
Asian Journal of Chemistry,
Vol. 30 No. 8 (2018): Vol 30 Issue 8
Abstract
Biological important ternary complexes of type [HgL(A-A)] [where L = 2-(2'-hydroxynaphthyl)benzothiazole (APBT), 2-(2'-hydroxyphenyl)benzothiazole (HPBT), 2-(2'-mercapto-phenyl)benzothiazole (MPBT)] (A = glycine or alanine) have been synthesized and characterized by m.w. determination, magnetic measurements, infrared and NMR studies. A tetrahedral geometry has been proposed for the present mercury(II) complexes. All the complexes are coloured, thermally stable, monomeric and non-electrolytic in nature. The ligands and their metal complexes showed biological activity against pathogenic fungi Aspergillus niger and Fusarium oxysporum. The antifungal activity data revealed that mercury(II) complexes are found more fungi-toxic than the parent ligands.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- C.Q. Xu, Z.C. Zhang and Q.Ye, Mater. Lett., 58, 1671 (2004); https://doi.org/10.1016/j.matlet.2003.11.005.
- P.S. Nair, T. Radhakrishnan, N. Revaprasadu, G.A. Kolawole and P.O'. Brien, J. Mater. Chem., 14, 581 (2004); https://doi.org/10.1039/B304098B.
- A. Askarinejad and A. Morsali, Chem. Eng. J., 153, 183 (2009); https://doi.org/10.1016/j.cej.2009.05.031.
- M.H. Huang, S. Mao, H. Feick, H. Yan, Y. Wu, H. Kind, E. Weber, R. Russo and P. Yang, Science, 292, 1897 (2001); https://doi.org/10.1126/science.1060367.
- B.V. Cheesman, A.P. Arnold and D.L. Rabenstein, J. Am. Chem. Soc., 110, 6359 (1988); https://doi.org/10.1021/ja00227a014.
- H. Razavi, S.K. Palaninathan, E.T. Powers, R.L. Wiseman, H.E. Purkey, N.N. Mohamedmohaideen, S. Deechongkit, K.P. Chiang, M.T.A. Dendle, J.C. Sacchettini and J.W. Kelly, Angew. Chem., Int. Ed., 42, 2758 (2003); https://doi.org/10.1002/anie.200351179.
- M.S. Malamas, E.S. Manas, R.E. McDevitt, I. Gunawan, Z.B. Xu, M.D. Collini, C.P. Miller, T. Dinh, R.A. Henderson, J.C. Keith and H.A. Harris, J. Med. Chem., 47, 5021 (2004); https://doi.org/10.1021/jm049719y.
- M. Taki, J.L. Wolford and T.V. O'Halloran, J. Am. Chem. Soc., 126, 712 (2004); https://doi.org/10.1021/ja039073j.
- S. Ueda and H. Nagasawa, Angew. Chem., Int. Ed., 47, 6411 (2008); https://doi.org/10.1002/anie.200801240.
- I.H. Leaver and B. Milligan, Dyes Pigments, 5, 109 (1984); https://doi.org/10.1016/0143-7208(84)80008-X.
- J.P. Davidson an E.J. Corey, J. Am. Chem. Soc., 125, 13486 (2003); https://doi.org/10.1021/ja0378916.
- D.C. Tully, H. Liu, P.B. Alper, A.K. Chatterjee, R. Epple, M.J. Roberts, J.A. Williams, K.T. Nguyen, D.H. Woodmansee, C. Tumanut, J. Li, G. Spraggon, J. Chang, T. Tuntland, J.L. Harris and D.S. Karanewsky, Bioorg. Med. Chem. Lett., 16, 1975 (2006); https://doi.org/10.1016/j.bmcl.2005.12.095.
- J.A. Grobler, G. Dornadula, R.M. Rice, A.L. Simcoe, D.J. Hazuda and M.D. Miller, J. Biol. Chem., 282, 8005 (2007); https://doi.org/10.1074/jbc.M608274200.
- L. Leventhal, M.R. Brandt, T.A. Cummons, M.J. Piesla, K.E. Rogers and H.A. Harris, Eur. J. Pharmacol., 553, 146 (2006); https://doi.org/10.1016/j.ejphar.2006.09.033.
- J. Nishiu, M. Ito, Y. Ishida, M. Kakutani, T. Shibata, M. Matsushita and M. Shindo, Diabetes Obes. Metab., 8, 508 (2006); https://doi.org/10.1111/j.1463-1326.2005.00536.x.
- J. Easmon, G. Pürstinger, K. S. Thies, G. Heinisch and J. Hofmann, J. Med. Chem., 49, 6343 (2006); https://doi.org/10.1021/jm060232u.
- S. Ohrui, N. Yamamoto, T. Saitoha, N. Kutsumura, Y. Nagumo, Y. IrukayamaTomobe, Y. Ogawa, Y. Ishikawa, Y. Watanabe, D. Hayakawa, H. Gouda, M. Yanagisawa and H. Nagase, Bioorg. Med. Chem., 28, 774 (2018); https://doi.org/10.1016/j.bmcl.2017.12.069.
- R.S. Srivastava, Indian J. Chem., 29A, 1024 (1990).
- A.S. Demir, H. Hamamci, O. Sesenoglu, R. Neslihanoglu, B. Asikoglu and D. Capanoglu, Tetrahedron Lett., 43, 6447 (2002); https://doi.org/10.1016/S0040-4039(02)01362-X.
- P.C. Vyas, Y.K. Chahar, Y. Garg and G. Seth, J. Indian Chem. Soc., 80, 843 (2003).
- L.S. Sbirna, V. Muresan, S. Sbirna and N. Muresan, J. Indian Chem. Soc., 82, 389 (2005).
- B. Ulkuseven and A. Tavman, Transition Met. Chem., 26, 723 (2001); https://doi.org/10.1023/A:1012033229710.
- N. Pal, R. Upadhyay and P.K. Pandey, Int. J. ChemTech Res., 10, 321 (2017).
- A. Heyrovský, Analyst, 85, 432 (1960); https://doi.org/10.1039/AN9608500432.
- S. Sarkar, P.K. Dhara, M. Nethaji and P. Chattopadhyay, J. Coord. Chem., 62, 817 (2009); https://doi.org/10.1080/00958970802314951.
- A.M. Khedr and D.F. Draz, J. Coord. Chem., 63, 1418 (2010); https://doi.org/10.1080/00958971003774241.
- J.K. Swearingen, W. Kaminsky and D.X. West, Transition Met. Chem., 27, 724 (2002); https://doi.org/10.1023/A:1020311408821.
- V. Philip, V. Suni and M.R.P. Kurup, Acta Cryst. C, 60, o856 (2004); https://doi.org/10.1107/S0108270104025235.
- P.P. Hankare, L.V. Gavali, V.M. Bhuse, S.D. Delekar and R.S. Rokade, Indian J. Chem., 43A, 2578 (2004).
- A. Patra, S. Sarkar, R. Chakraborty, M.G.B. Drew and P. Chattopadhyay, J. Coord. Chem., 63, 1913 (2010); https://doi.org/10.1080/00958972.2010.495985.
- I.I. Kasher, A.S. E1-Tabl and R.M. E1-Bahnasawy, Polish J. Chem., 729, 2037 (1998).
- M. Sonmez and M. Sekerci, Synth. React. Inorg. Met.-Org. Chem., 34, 489 (2004); https://doi.org/10.1081/SIM-120030436.
- M. Sonmez, M.R. Bayram and M. Celebi, J. Coord. Chem., 62, 2728 (2009); https://doi.org/10.1080/00958970902915582.
- T.T. Bamgboye and O.A. Bamgboye, Inorg. Chim. Acta, 133, 247 (1987); https://doi.org/10.1016/S0020-1693(00)87774-9.
- D.W. Heins, R.J. Alheim and J. Leavitt, J. Am. Chem. Soc., 79, 427 (1957); https://doi.org/10.1021/ja01559a053.
- M. Vaara, Microbiol. Rev., 56, 395 (1992).
- H.-L. Alakomi, A. Paananen, M.-L. Suihko, I.M. Helander and M. Saarela, Appl. Environ. Microbiol., 72, 4695 (2006); https://doi.org/10.1128/AEM.00142-06.
References
C.Q. Xu, Z.C. Zhang and Q.Ye, Mater. Lett., 58, 1671 (2004); https://doi.org/10.1016/j.matlet.2003.11.005.
P.S. Nair, T. Radhakrishnan, N. Revaprasadu, G.A. Kolawole and P.O'. Brien, J. Mater. Chem., 14, 581 (2004); https://doi.org/10.1039/B304098B.
A. Askarinejad and A. Morsali, Chem. Eng. J., 153, 183 (2009); https://doi.org/10.1016/j.cej.2009.05.031.
M.H. Huang, S. Mao, H. Feick, H. Yan, Y. Wu, H. Kind, E. Weber, R. Russo and P. Yang, Science, 292, 1897 (2001); https://doi.org/10.1126/science.1060367.
B.V. Cheesman, A.P. Arnold and D.L. Rabenstein, J. Am. Chem. Soc., 110, 6359 (1988); https://doi.org/10.1021/ja00227a014.
H. Razavi, S.K. Palaninathan, E.T. Powers, R.L. Wiseman, H.E. Purkey, N.N. Mohamedmohaideen, S. Deechongkit, K.P. Chiang, M.T.A. Dendle, J.C. Sacchettini and J.W. Kelly, Angew. Chem., Int. Ed., 42, 2758 (2003); https://doi.org/10.1002/anie.200351179.
M.S. Malamas, E.S. Manas, R.E. McDevitt, I. Gunawan, Z.B. Xu, M.D. Collini, C.P. Miller, T. Dinh, R.A. Henderson, J.C. Keith and H.A. Harris, J. Med. Chem., 47, 5021 (2004); https://doi.org/10.1021/jm049719y.
M. Taki, J.L. Wolford and T.V. O'Halloran, J. Am. Chem. Soc., 126, 712 (2004); https://doi.org/10.1021/ja039073j.
S. Ueda and H. Nagasawa, Angew. Chem., Int. Ed., 47, 6411 (2008); https://doi.org/10.1002/anie.200801240.
I.H. Leaver and B. Milligan, Dyes Pigments, 5, 109 (1984); https://doi.org/10.1016/0143-7208(84)80008-X.
J.P. Davidson an E.J. Corey, J. Am. Chem. Soc., 125, 13486 (2003); https://doi.org/10.1021/ja0378916.
D.C. Tully, H. Liu, P.B. Alper, A.K. Chatterjee, R. Epple, M.J. Roberts, J.A. Williams, K.T. Nguyen, D.H. Woodmansee, C. Tumanut, J. Li, G. Spraggon, J. Chang, T. Tuntland, J.L. Harris and D.S. Karanewsky, Bioorg. Med. Chem. Lett., 16, 1975 (2006); https://doi.org/10.1016/j.bmcl.2005.12.095.
J.A. Grobler, G. Dornadula, R.M. Rice, A.L. Simcoe, D.J. Hazuda and M.D. Miller, J. Biol. Chem., 282, 8005 (2007); https://doi.org/10.1074/jbc.M608274200.
L. Leventhal, M.R. Brandt, T.A. Cummons, M.J. Piesla, K.E. Rogers and H.A. Harris, Eur. J. Pharmacol., 553, 146 (2006); https://doi.org/10.1016/j.ejphar.2006.09.033.
J. Nishiu, M. Ito, Y. Ishida, M. Kakutani, T. Shibata, M. Matsushita and M. Shindo, Diabetes Obes. Metab., 8, 508 (2006); https://doi.org/10.1111/j.1463-1326.2005.00536.x.
J. Easmon, G. Pürstinger, K. S. Thies, G. Heinisch and J. Hofmann, J. Med. Chem., 49, 6343 (2006); https://doi.org/10.1021/jm060232u.
S. Ohrui, N. Yamamoto, T. Saitoha, N. Kutsumura, Y. Nagumo, Y. IrukayamaTomobe, Y. Ogawa, Y. Ishikawa, Y. Watanabe, D. Hayakawa, H. Gouda, M. Yanagisawa and H. Nagase, Bioorg. Med. Chem., 28, 774 (2018); https://doi.org/10.1016/j.bmcl.2017.12.069.
R.S. Srivastava, Indian J. Chem., 29A, 1024 (1990).
A.S. Demir, H. Hamamci, O. Sesenoglu, R. Neslihanoglu, B. Asikoglu and D. Capanoglu, Tetrahedron Lett., 43, 6447 (2002); https://doi.org/10.1016/S0040-4039(02)01362-X.
P.C. Vyas, Y.K. Chahar, Y. Garg and G. Seth, J. Indian Chem. Soc., 80, 843 (2003).
L.S. Sbirna, V. Muresan, S. Sbirna and N. Muresan, J. Indian Chem. Soc., 82, 389 (2005).
B. Ulkuseven and A. Tavman, Transition Met. Chem., 26, 723 (2001); https://doi.org/10.1023/A:1012033229710.
N. Pal, R. Upadhyay and P.K. Pandey, Int. J. ChemTech Res., 10, 321 (2017).
A. Heyrovský, Analyst, 85, 432 (1960); https://doi.org/10.1039/AN9608500432.
S. Sarkar, P.K. Dhara, M. Nethaji and P. Chattopadhyay, J. Coord. Chem., 62, 817 (2009); https://doi.org/10.1080/00958970802314951.
A.M. Khedr and D.F. Draz, J. Coord. Chem., 63, 1418 (2010); https://doi.org/10.1080/00958971003774241.
J.K. Swearingen, W. Kaminsky and D.X. West, Transition Met. Chem., 27, 724 (2002); https://doi.org/10.1023/A:1020311408821.
V. Philip, V. Suni and M.R.P. Kurup, Acta Cryst. C, 60, o856 (2004); https://doi.org/10.1107/S0108270104025235.
P.P. Hankare, L.V. Gavali, V.M. Bhuse, S.D. Delekar and R.S. Rokade, Indian J. Chem., 43A, 2578 (2004).
A. Patra, S. Sarkar, R. Chakraborty, M.G.B. Drew and P. Chattopadhyay, J. Coord. Chem., 63, 1913 (2010); https://doi.org/10.1080/00958972.2010.495985.
I.I. Kasher, A.S. E1-Tabl and R.M. E1-Bahnasawy, Polish J. Chem., 729, 2037 (1998).
M. Sonmez and M. Sekerci, Synth. React. Inorg. Met.-Org. Chem., 34, 489 (2004); https://doi.org/10.1081/SIM-120030436.
M. Sonmez, M.R. Bayram and M. Celebi, J. Coord. Chem., 62, 2728 (2009); https://doi.org/10.1080/00958970902915582.
T.T. Bamgboye and O.A. Bamgboye, Inorg. Chim. Acta, 133, 247 (1987); https://doi.org/10.1016/S0020-1693(00)87774-9.
D.W. Heins, R.J. Alheim and J. Leavitt, J. Am. Chem. Soc., 79, 427 (1957); https://doi.org/10.1021/ja01559a053.
M. Vaara, Microbiol. Rev., 56, 395 (1992).
H.-L. Alakomi, A. Paananen, M.-L. Suihko, I.M. Helander and M. Saarela, Appl. Environ. Microbiol., 72, 4695 (2006); https://doi.org/10.1128/AEM.00142-06.