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Synthesis, Biological Evaluation and Molecular Modeling Study of 3,4-Disubstituted 5-Mercapto-1,2,4-triazoles
Corresponding Author(s) : Subhas Sahoo
Asian Journal of Chemistry,
Vol. 28 No. 3 (2016): Vol 28 Issue 3
Abstract
Based on the outcome of computational docking to the active site of cytochrome P450 14a-demethylase (CYP51), diverse 3,4-disubstituted 5-mercapto-1,2,4-triazoles were prepared and screened for antioxidant and antifungal activities. The docking study of synthesized compounds showed promising binding affinity towards docked enzyme, sterol 14a-demethylase(CYP51) from trypanosome cruzi obtained from a RCSB protein data bank (PDB ID: 3KHM). The synthesized compounds were characterized by IR, 1H NMR and Mass spectral data. Among the novel synthesized compounds IV-6, IV-1 and IV-2 showed maximum antifungal activity against A. niger and C. albicans organism when compared the standard fluconazole. For antioxidant activity, all the compounds showed moderate activity but compound IV-6 and IV-7 showed significant activity when compared to standard ascorbic acid.
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- C. Kuş, G. Ayhan-Kilcigil, S. Özbey, F.B. Kaynak, M. Kaya, T. Çoban and B. Can-Eke, Bioorg. Med. Chem., 16, 4294 (2008); doi:10.1016/j.bmc.2008.02.077.
- B. Halliwell, J.M. Gutteridge and C.E. Cross, J. Lab. Clin. Med., 119, 598 (1992).
- L. Yu, S. Haley, J. Perret, M. Harris, J. Wilson and M. Qian, J. Agric. Food Chem., 50, 1619 (2002); doi:10.1021/jf010964p.
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- M.W. Khan, M.J. Alam, M.A. Rashid and R. Chowdhury, Bioorg. Med. Chem., 13, 4796 (2005); doi:10.1016/j.bmc.2005.05.009.
- M. Hogberg, P. Engelhardt, L. Vrang and H. Zhang, Bioorg. Med. Chem. Lett., 10, 265 (2000); doi:10.1016/S0960-894X(99)00675-7.
- Y. Dong, T.K. Venkatachalam, R.K. Narla, V.N. Trieu, E.A. Sudbeck and F.M. Uckun, Bioorg. Med. Chem. Lett., 10, 87 (2000); doi:10.1016/S0960-894X(99)00581-8.
- G. Mazzone, F. Bonina, R. Arrigo and G. Blandino, Farmaco Sci., 36, 181 (1981).
- S. Narayanaswami and K. Richardson, European Patent, 96,569 (1983); Chem. Abstr., 100, 139122t (1984).
- M.B. Gravestock, European Patent, 94,146 (1983); Chem. Abstr., 100, 139118w (1984).
- E. De Clercq, J. Clin. Virol., 30, 115 (2004); doi:10.1016/j.jcv.2004.02.009.
- L. Navidpour, H. Shadnia, H. Shafaroodi, M. Amini, A.R. Dehpour and A. Shafiee, Bioorg. Med. Chem., 15, 1976 (2007); doi:10.1016/j.bmc.2006.12.041.
- N.H. Georgopapadakou and T.J. Walsh , Antimicrob. Agents Chemother., 40, 279 (1996).
- S. Sahoo, P.K. Patwari, C.B. Mahender Kumar and C.M. Setty, Iranian J. Pharm. Sci., 9, 51 (2013).
- M. Koparir, A. Cansiz and A. Demirdag, Molecules, 9, 204 (2004); doi:10.3390/90400204.
- A. Braca, N. De Tommasi, L. Di Bari, C. Pizza, M. Politi and I. Morelli, J. Nat. Prod., 64, 892 (2001); doi:10.1021/np0100845.
- O. Trott and A.J. Olson, J. Computational Chem., 31, 455 (2010); doi:10.1002/jcc.21334.
- National Committee for Clinical Laboratory Standards (NCCLS), Performance Standards for Antimicrobial Disk Susceptibility Tests: Approved Standard M2-A6, National Committee for Clinical Laboratory Standards, Wayne, PA, edn 6 (1999).
References
C. Kuş, G. Ayhan-Kilcigil, S. Özbey, F.B. Kaynak, M. Kaya, T. Çoban and B. Can-Eke, Bioorg. Med. Chem., 16, 4294 (2008); doi:10.1016/j.bmc.2008.02.077.
B. Halliwell, J.M. Gutteridge and C.E. Cross, J. Lab. Clin. Med., 119, 598 (1992).
L. Yu, S. Haley, J. Perret, M. Harris, J. Wilson and M. Qian, J. Agric. Food Chem., 50, 1619 (2002); doi:10.1021/jf010964p.
K.A. Metwally, L.M. Abdel-Aziz, E.-S.M. Lashine, M.I. Husseiny and R.H. Badawy, Bioorg. Med. Chem., 14, 8675 (2006); doi:10.1016/j.bmc.2006.08.022.
M.W. Khan, M.J. Alam, M.A. Rashid and R. Chowdhury, Bioorg. Med. Chem., 13, 4796 (2005); doi:10.1016/j.bmc.2005.05.009.
M. Hogberg, P. Engelhardt, L. Vrang and H. Zhang, Bioorg. Med. Chem. Lett., 10, 265 (2000); doi:10.1016/S0960-894X(99)00675-7.
Y. Dong, T.K. Venkatachalam, R.K. Narla, V.N. Trieu, E.A. Sudbeck and F.M. Uckun, Bioorg. Med. Chem. Lett., 10, 87 (2000); doi:10.1016/S0960-894X(99)00581-8.
G. Mazzone, F. Bonina, R. Arrigo and G. Blandino, Farmaco Sci., 36, 181 (1981).
S. Narayanaswami and K. Richardson, European Patent, 96,569 (1983); Chem. Abstr., 100, 139122t (1984).
M.B. Gravestock, European Patent, 94,146 (1983); Chem. Abstr., 100, 139118w (1984).
E. De Clercq, J. Clin. Virol., 30, 115 (2004); doi:10.1016/j.jcv.2004.02.009.
L. Navidpour, H. Shadnia, H. Shafaroodi, M. Amini, A.R. Dehpour and A. Shafiee, Bioorg. Med. Chem., 15, 1976 (2007); doi:10.1016/j.bmc.2006.12.041.
N.H. Georgopapadakou and T.J. Walsh , Antimicrob. Agents Chemother., 40, 279 (1996).
S. Sahoo, P.K. Patwari, C.B. Mahender Kumar and C.M. Setty, Iranian J. Pharm. Sci., 9, 51 (2013).
M. Koparir, A. Cansiz and A. Demirdag, Molecules, 9, 204 (2004); doi:10.3390/90400204.
A. Braca, N. De Tommasi, L. Di Bari, C. Pizza, M. Politi and I. Morelli, J. Nat. Prod., 64, 892 (2001); doi:10.1021/np0100845.
O. Trott and A.J. Olson, J. Computational Chem., 31, 455 (2010); doi:10.1002/jcc.21334.
National Committee for Clinical Laboratory Standards (NCCLS), Performance Standards for Antimicrobial Disk Susceptibility Tests: Approved Standard M2-A6, National Committee for Clinical Laboratory Standards, Wayne, PA, edn 6 (1999).