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Synthesis, SAR, Molecular Docking and Antituberculosis Study of 3-Methyl-1-Benzofuran-2-Carbohydrazide
Corresponding Author(s) : Bapu R. Thorat
Asian Journal of Chemistry,
Vol. 28 No. 11 (2016): Vol 28 Issue 11
Abstract
3-Methyl-1-benzofuran-2-carbohydrazide was synthesized from 2-hydroxy acetophenone. To deduce the antibacterial and anticancer activity of the 3-methyl-1-benzofuran-2-carbohydrazide, it is docked with different biomarkers of cancer cell and bacteria. The binding model of best scoring analogue with each protein was assessed from their G-scores and disclosed by docking analysis using the XP visualizer tool. An analysis of the receptor-ligand interaction studies revealed that 3-methyl-1-benzofuran-2-carbohydrazide is most active against 3LAU (Arora 2 kinase) and 1VOM (Dictyostelium myosin) biomarkers and have the features to prove themselves as antituberculosis drugs. The structure of the target molecule compared with ciprofloxacin (antituberculosis drug) and shows 67.4 % structural similarity. Cramer rules of toxicity predicts the toxicological hazard (when administered orally) from the molecular structure. It shows that it is class III toxic compound. The antituberculosis studies show that it shows strong activity (1.6 μg/mL) against mycobacterium tuberculosis (H37 RV strain).
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- P.K. Mahakhud and M.R. Parthasarathy, Indian J. Chem., 34B, 713 (1995); B.R. Thorat, D. Shelke, R.G. Atram and R.S. Yamgar, Heterocycl. Lett., 3, 385 (2013).
- G. Samuelsson, Drugs of Natural Origin, Swedish Pharmaceutical, Stockholm (1992); B.R. Thorat, D. Shelke, R.G. Atram and R.S. Yamgar, Heterocycl. Lett., 3, 331 (2013); B.R. Thorat, S. Shelke, R. Jagtap and R.S. Yamgar, Heterocycl. Lett., 4, 321 (2014).
- J.W. Mason, N. Eng. J. Med., 316, 455 (1987); doi:10.1056/NEJM198702193160807.
- G.N. Walker and R.T. Smith, J. Org. Chem., 36, 305 (1971); doi:10.1021/jo00801a013.
- M. Mandewale, B.R. Thorat, B. Nazirkar, V.B. Thorat, A. Nagarsekar and R.S. Yamgar, J. Chem. Sci., 110, 279 (2016).
- R. Madhu and M.D. Karvekar, Int. J. Pharm. Pharm. Sci., 2, 6466 (2010).
- G. Parameshwarappa, B. Raga, S.O. Khandre and S.S. Sangapure, Heterocycl. Commun., 15, 335 (2009); doi:10.1515/HC.2009.15.5.335.
- A.R. Leach, Molecular Modelling: Principles and Applications, Pearson Education EMA, edn 2 (2001); B.R. Thorat, R. Jagtap, V.B. Thorat, A. Khemanar and R.S. Yamgar, Heterocycl. Lett., 5, 59 (2015); B.R. Thorat, R. Jagtap, V.B. Thorat, A. Khemanar and R.S. Yamgar, Int. J. Comput. Bioinfo. In Silico Model,4, 597 (2015); B.R. Thorat, R. Jagtap, V.B. Thorat, A. Khemanar and R.S. Yamgar, Der Pharma Chemica, 7,169 (2015); B.R. Thorat, R. Jagatap, A.S. Nagarsekar,V.B. Thorat and R.S. Yamgar, J. Adv. Bioinformatics Appl. Res., 6, 62 (2015).
- E.M. Gordon M.A. Gallop and D.V. Patel, Acc. Chem. Res., 29, 144 (1996); doi:10.1021/ar950170u.
- P.B. Fernandes, Curr. Opin. Chem. Biol., 2, 597 (1998).
- R.P. Hertzberg and A.J. Pope, Curr. Opin. Chem. Biol., 4, 445 (2000).
- D.E. Clark, Ann. Rep. Comput. Chem., 1, 133 (2005).
- B.R. Thorat, M. Mandewale, S. Shelke, P. Kamat, R.G. Atram, M. Bhalerao and R. Yamgar, J. Chem. Pharm. Res., 4, 14 (2012).
- B. Thorat, V. Ahuja, M. Mandewale, R. Yamgar and L.V. Gavali, World J. Pharm. Res., 4, 2250 (2015).
References
P.K. Mahakhud and M.R. Parthasarathy, Indian J. Chem., 34B, 713 (1995); B.R. Thorat, D. Shelke, R.G. Atram and R.S. Yamgar, Heterocycl. Lett., 3, 385 (2013).
G. Samuelsson, Drugs of Natural Origin, Swedish Pharmaceutical, Stockholm (1992); B.R. Thorat, D. Shelke, R.G. Atram and R.S. Yamgar, Heterocycl. Lett., 3, 331 (2013); B.R. Thorat, S. Shelke, R. Jagtap and R.S. Yamgar, Heterocycl. Lett., 4, 321 (2014).
J.W. Mason, N. Eng. J. Med., 316, 455 (1987); doi:10.1056/NEJM198702193160807.
G.N. Walker and R.T. Smith, J. Org. Chem., 36, 305 (1971); doi:10.1021/jo00801a013.
M. Mandewale, B.R. Thorat, B. Nazirkar, V.B. Thorat, A. Nagarsekar and R.S. Yamgar, J. Chem. Sci., 110, 279 (2016).
R. Madhu and M.D. Karvekar, Int. J. Pharm. Pharm. Sci., 2, 6466 (2010).
G. Parameshwarappa, B. Raga, S.O. Khandre and S.S. Sangapure, Heterocycl. Commun., 15, 335 (2009); doi:10.1515/HC.2009.15.5.335.
A.R. Leach, Molecular Modelling: Principles and Applications, Pearson Education EMA, edn 2 (2001); B.R. Thorat, R. Jagtap, V.B. Thorat, A. Khemanar and R.S. Yamgar, Heterocycl. Lett., 5, 59 (2015); B.R. Thorat, R. Jagtap, V.B. Thorat, A. Khemanar and R.S. Yamgar, Int. J. Comput. Bioinfo. In Silico Model,4, 597 (2015); B.R. Thorat, R. Jagtap, V.B. Thorat, A. Khemanar and R.S. Yamgar, Der Pharma Chemica, 7,169 (2015); B.R. Thorat, R. Jagatap, A.S. Nagarsekar,V.B. Thorat and R.S. Yamgar, J. Adv. Bioinformatics Appl. Res., 6, 62 (2015).
E.M. Gordon M.A. Gallop and D.V. Patel, Acc. Chem. Res., 29, 144 (1996); doi:10.1021/ar950170u.
P.B. Fernandes, Curr. Opin. Chem. Biol., 2, 597 (1998).
R.P. Hertzberg and A.J. Pope, Curr. Opin. Chem. Biol., 4, 445 (2000).
D.E. Clark, Ann. Rep. Comput. Chem., 1, 133 (2005).
B.R. Thorat, M. Mandewale, S. Shelke, P. Kamat, R.G. Atram, M. Bhalerao and R. Yamgar, J. Chem. Pharm. Res., 4, 14 (2012).
B. Thorat, V. Ahuja, M. Mandewale, R. Yamgar and L.V. Gavali, World J. Pharm. Res., 4, 2250 (2015).