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Synthesis and Characterization of Ester Derivatives of N-Phenylanthranilic Acid
Corresponding Author(s) : Madhu Bala
Asian Journal of Chemistry,
Vol. 36 No. 10 (2024): Vol 36 Issue 10, 2024
Abstract
N-Phenylanthranilic acid (fenamic acid) serves as the fundamental structure for synthesizing several non-steroidal anti-inflammatory drugs, antibacterial drugs and also functions as a modulator of membrane transport. To reduce the dose-related side effects of existing drugs, research is focussing to improve fenamic acid derivative solubility and bioavailability. A series of ester derivatives of N-phenylanthranilic acid (MB-1 to MB-5) viz. 2-(phenyl amino)methyl benzoate, 2-(phenyl amino)ethyl benzoate, 2-(phenyl amino)isopropyl benzoate,
2-(phenyl amino)butyl benzoate and 2-(phenyl amino)phenyl benzoate were synthesized. The chemical structures and functional groups of these derivatives were confirmed using elemental analysis and spectral data. Furthermore, the derived compounds were evaluated for their antibacterial activity against Escherichia coli (Gram-negative) and Staphylococcus aureus (Gram-positive) strains using the agar-well diffusion method followed by molecular docking studies to predict binding interactions of the synthesized compounds with DNA gyrase.
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- P. Wiklund and J. Bergman, Curr. Org. Synth., 3, 379 (2006); https://doi.org/10.2174/157017906777934926
- P. Prasher and M. Sharma, Drug Dev. Res., 82, 945 (2021); https://doi.org/10.1002/ddr.21842
- T. Nasr, A. Aboshanab, K. Abouzid and W. Zaghary, Egypt. J. Chem., 66, 329 (2022); https://doi.org/10.21608/ejchem.2022.148409.6426
- R.E. Williams, L. Cottrell, M. Jacobsen, L.R. Bandara, M.D. Kelly, S. Kennedy and E.A. Lock, Biomarkers, 8, 472 (2003); https://doi.org/10.1080/13547500310001647030
- H. Azuma, K. Banno and T. Yoshimura, Br. J. Pharmacol., 58, 483 (1976); https://doi.org/10.1111/j.1476-5381.1976.tb08614.x
- I.-S. Kwon, J.H. Kwak, S. Pyo, H.-W. Lee, A. Kim and F.J. Schmitz, J. Nat. Prod., 80, 149 (2017); https://doi.org/10.1021/acs.jnatprod.6b00787
- H. Schrey, F.J. Müller, P. Harz, Z. Rupcic, M. Stadler and P. Spiteller, Phytochemistry, 160, 85 (2019); https://doi.org/10.1016/j.phytochem.2019.01.008
- R. Teponno, S. Noumeur, S. Helaly, S. Hüttel, D. Harzallah and M. Stadler, Molecules, 22, 1674 (2017); https://doi.org/10.3390/molecules22101674
- F. Omar, N. Mahfouz and M. Rahman, Eur. J. Med. Chem., 31, 819 (1996); https://doi.org/10.1016/0223-5234(96)83976-6
- H. Jiang, B. Zeng, G.-L. Chen, D. Bot, S. Eastmond, S.E. Elsenussi, S.L. Atkin, A.N. Boa and S.-Z. Xu, Biochem. Pharmacol., 83, 923 (2012); https://doi.org/10.1016/j.bcp.2012.01.014
- M.C.P. Rees, R. Cañete-Solér, A. López Bernal and A.C. Turnbull, Lancet, 332, 541 (1988); https://doi.org/10.1016/s0140-6736(88)92660-8.
- M.K. Elgohary, M.S. Elkotamy, M.A. Alkabbani and H.A. Abdel-Aziz. Bioorg. Chem., 147, 107393 (2024); https://doi.org/10.1016/j.bioorg.2024.107393
- A.P. Malykhina, F. Shoeb and H.I. Akbarali, Eur. J. Pharmacol., 452, 269 (2002); https://doi.org/10.1016/S0014-2999(02)02330-0
- T. Suzuki, A. Hansen and M.C. Sanguinetti, Biochim. Biophys. Acta Biomembr., 1858, 783 (2016); https://doi.org/10.1016/j.bbamem.2015.12.024
- P. Garg, Biophys. J., 104, 463A (2013); https://doi.org/10.1016/j.bpj.2012.11.2562
- H. Hu, J. Tian, Y. Zhu, C. Wang, R. Xiao, J.M. Herz, J.D. Wood and M.X. Zhu, Pflugers Arch., 459, 579 (2010); https://doi.org/10.1007/s00424-009-0749-9
- C. Klose, I. Straub, M. Riehle, F. Ranta, D. Krautwurst, S. Ullrich, W. Meyerhof and C. Harteneck, Br. J. Pharmacol., 162, 1757 (2011); https://doi.org/10.1111/j.1476-5381.2010.01186.x
- J.-F. Sun, Y.-J. Xu, X.-H. Kong, Y. Su and Z.-Y. Wang, Neurosci. Lett., 696, 67 (2019); https://doi.org/10.1016/j.neulet.2018.12.008
- K. Yamada, Y. Waniishi, R. Inoue and Y. Ito, Japan. J. Pharmacol., 70, 81 (1996); https://doi.org/10.1254/jjp.70.81
- F. Buttgereit, G.R. Burmester and L.S. Simon, Am. J. Med., 110, 13 (2001); https://doi.org/10.1016/S0002-9343(00)00728-2
- K.A. Metwally, S.H. Yaseen, E.-S.M. Lashine, H.M. El-Fayomi and M.E. El-Sadek, Eur. J. Med. Chem., 42, 152 (2007); https://doi.org/10.1016/j.ejmech.2006.09.001
- S. Bala, S. Kamboj, V. Saini and D.N. Prasad, J. Chem., 2013, 412043 (2013); https://doi.org/10.1155/2013/412053
- A. Husain, M.S.Y. Khan, S.M. Hasan and M.M. Alam, Eur. J. Med. Chem., 40, 1394 (2005); https://doi.org/10.1016/j.ejmech.2005.03.012
- F.L. Lanza, Am. J. Gastroenterol., 93, 2037 (1998); https://doi.org/10.1111/j.1572-0241.1998.00588.x
- M.P. Gleeson, A. Hersey and S. Hannongbua, Curr. Top. Med. Chem., 11, 358 (2011); https://doi.org/10.2174/156802611794480927
- A. Daina, O. Michielin and V. Zoete, Sci. Rep., 7, 42717 (2017); https://doi.org/10.1038/srep42717
- C.A. Lipinski, Drug Discov. Today Technol., 1, 337 (2004); https://doi.org/10.1016/j.ddtec.2004.11.007
- H. Berman, K. Henrick and H. Nakamura, Nat. Struct. Mol. Biol., 10, 980 (2003); https://doi.org/10.1038/nsb1203-980
- G.M. Morris, R. Huey, W. Lindstrom, M.F. Sanner, R.K. Belew, D.S. Goodsell and A.J. Olson, J. Comput. Chem., 30, 2785 (2009); https://doi.org/10.1002/jcc.21256
- O. Trott and A.J. Olson, J. Comput. Chem., 31, 455 (2010); https://doi.org/10.1002/jcc.21334
- D.E. Pires, T.L. Blundell and D.B. Ascher, J. Med. Chem., 58, 4066 (2015); https://doi.org/10.1021/acs.jmedchem.5b00104
- A.C.F. Salgueiro, V. Folmer, H.S. da Rosa, M.T. Costa, A.A. Boligon, F.R. Paula, D.H. Roos and G.O. Puntel, J. Ethnopharmacol., 194, 6 (2016); https://doi.org/10.1016/j.jep.2016.08.048
- D.E.V. Pires, L.M. Kaminskas and D.B. Ascher, Methods Mol. Biol., 1762, 271 (2018); https://doi.org/10.1007/978-1-4939-7756-7_14
References
P. Wiklund and J. Bergman, Curr. Org. Synth., 3, 379 (2006); https://doi.org/10.2174/157017906777934926
P. Prasher and M. Sharma, Drug Dev. Res., 82, 945 (2021); https://doi.org/10.1002/ddr.21842
T. Nasr, A. Aboshanab, K. Abouzid and W. Zaghary, Egypt. J. Chem., 66, 329 (2022); https://doi.org/10.21608/ejchem.2022.148409.6426
R.E. Williams, L. Cottrell, M. Jacobsen, L.R. Bandara, M.D. Kelly, S. Kennedy and E.A. Lock, Biomarkers, 8, 472 (2003); https://doi.org/10.1080/13547500310001647030
H. Azuma, K. Banno and T. Yoshimura, Br. J. Pharmacol., 58, 483 (1976); https://doi.org/10.1111/j.1476-5381.1976.tb08614.x
I.-S. Kwon, J.H. Kwak, S. Pyo, H.-W. Lee, A. Kim and F.J. Schmitz, J. Nat. Prod., 80, 149 (2017); https://doi.org/10.1021/acs.jnatprod.6b00787
H. Schrey, F.J. Müller, P. Harz, Z. Rupcic, M. Stadler and P. Spiteller, Phytochemistry, 160, 85 (2019); https://doi.org/10.1016/j.phytochem.2019.01.008
R. Teponno, S. Noumeur, S. Helaly, S. Hüttel, D. Harzallah and M. Stadler, Molecules, 22, 1674 (2017); https://doi.org/10.3390/molecules22101674
F. Omar, N. Mahfouz and M. Rahman, Eur. J. Med. Chem., 31, 819 (1996); https://doi.org/10.1016/0223-5234(96)83976-6
H. Jiang, B. Zeng, G.-L. Chen, D. Bot, S. Eastmond, S.E. Elsenussi, S.L. Atkin, A.N. Boa and S.-Z. Xu, Biochem. Pharmacol., 83, 923 (2012); https://doi.org/10.1016/j.bcp.2012.01.014
M.C.P. Rees, R. Cañete-Solér, A. López Bernal and A.C. Turnbull, Lancet, 332, 541 (1988); https://doi.org/10.1016/s0140-6736(88)92660-8.
M.K. Elgohary, M.S. Elkotamy, M.A. Alkabbani and H.A. Abdel-Aziz. Bioorg. Chem., 147, 107393 (2024); https://doi.org/10.1016/j.bioorg.2024.107393
A.P. Malykhina, F. Shoeb and H.I. Akbarali, Eur. J. Pharmacol., 452, 269 (2002); https://doi.org/10.1016/S0014-2999(02)02330-0
T. Suzuki, A. Hansen and M.C. Sanguinetti, Biochim. Biophys. Acta Biomembr., 1858, 783 (2016); https://doi.org/10.1016/j.bbamem.2015.12.024
P. Garg, Biophys. J., 104, 463A (2013); https://doi.org/10.1016/j.bpj.2012.11.2562
H. Hu, J. Tian, Y. Zhu, C. Wang, R. Xiao, J.M. Herz, J.D. Wood and M.X. Zhu, Pflugers Arch., 459, 579 (2010); https://doi.org/10.1007/s00424-009-0749-9
C. Klose, I. Straub, M. Riehle, F. Ranta, D. Krautwurst, S. Ullrich, W. Meyerhof and C. Harteneck, Br. J. Pharmacol., 162, 1757 (2011); https://doi.org/10.1111/j.1476-5381.2010.01186.x
J.-F. Sun, Y.-J. Xu, X.-H. Kong, Y. Su and Z.-Y. Wang, Neurosci. Lett., 696, 67 (2019); https://doi.org/10.1016/j.neulet.2018.12.008
K. Yamada, Y. Waniishi, R. Inoue and Y. Ito, Japan. J. Pharmacol., 70, 81 (1996); https://doi.org/10.1254/jjp.70.81
F. Buttgereit, G.R. Burmester and L.S. Simon, Am. J. Med., 110, 13 (2001); https://doi.org/10.1016/S0002-9343(00)00728-2
K.A. Metwally, S.H. Yaseen, E.-S.M. Lashine, H.M. El-Fayomi and M.E. El-Sadek, Eur. J. Med. Chem., 42, 152 (2007); https://doi.org/10.1016/j.ejmech.2006.09.001
S. Bala, S. Kamboj, V. Saini and D.N. Prasad, J. Chem., 2013, 412043 (2013); https://doi.org/10.1155/2013/412053
A. Husain, M.S.Y. Khan, S.M. Hasan and M.M. Alam, Eur. J. Med. Chem., 40, 1394 (2005); https://doi.org/10.1016/j.ejmech.2005.03.012
F.L. Lanza, Am. J. Gastroenterol., 93, 2037 (1998); https://doi.org/10.1111/j.1572-0241.1998.00588.x
M.P. Gleeson, A. Hersey and S. Hannongbua, Curr. Top. Med. Chem., 11, 358 (2011); https://doi.org/10.2174/156802611794480927
A. Daina, O. Michielin and V. Zoete, Sci. Rep., 7, 42717 (2017); https://doi.org/10.1038/srep42717
C.A. Lipinski, Drug Discov. Today Technol., 1, 337 (2004); https://doi.org/10.1016/j.ddtec.2004.11.007
H. Berman, K. Henrick and H. Nakamura, Nat. Struct. Mol. Biol., 10, 980 (2003); https://doi.org/10.1038/nsb1203-980
G.M. Morris, R. Huey, W. Lindstrom, M.F. Sanner, R.K. Belew, D.S. Goodsell and A.J. Olson, J. Comput. Chem., 30, 2785 (2009); https://doi.org/10.1002/jcc.21256
O. Trott and A.J. Olson, J. Comput. Chem., 31, 455 (2010); https://doi.org/10.1002/jcc.21334
D.E. Pires, T.L. Blundell and D.B. Ascher, J. Med. Chem., 58, 4066 (2015); https://doi.org/10.1021/acs.jmedchem.5b00104
A.C.F. Salgueiro, V. Folmer, H.S. da Rosa, M.T. Costa, A.A. Boligon, F.R. Paula, D.H. Roos and G.O. Puntel, J. Ethnopharmacol., 194, 6 (2016); https://doi.org/10.1016/j.jep.2016.08.048
D.E.V. Pires, L.M. Kaminskas and D.B. Ascher, Methods Mol. Biol., 1762, 271 (2018); https://doi.org/10.1007/978-1-4939-7756-7_14