Main Article Content
Abstract
In this work, pyrazole based oxothiazolidine hybrids, 4-{4-[2-(1-phenyl-3-(substituted)phenyl-1H-pyrazol-4-yl)-4-oxo-thiazolidin-3-yl]-phenyl}-morpholin-3-one (11a-l) were synthesized using molecular hybridization approach through Vilsmeier-Haack reaction. The titled compounds 11a-l were characterized by elemental analysis, IR, 1H NMR and mass spectral studies. The antibacterial activity of 11a-l was evaluated in vitro by agar cup plate method against B. cocous, B. subtillis, E. coli and P. vulgaris. The antifungal activity of compounds 11a-l was evaluated in vitro by agar based disk diffusion method against A. niger. The results of antibacterial and antifungal evaluation were reported in terms of zone of inhibition measured in mm. The synthesized compounds 11a-l exhibited moderate to good antibacterial and antifungal potential. Compound 4-{4-[2-(1-phenyl-3-(2-methoxyphenyl)phenyl-1H-pyrazol-4-yl)-4-oxo-thiazolidin-3-yl]-phenyl}-morpholin-3-one (11h) emerged as a most potent antimicrobial agent displaying zone of inhibition 21, 20, 21, 24 and 20 mm against B. cocous, B. subtillis, E. coli, P. vulgaris and A. niger, respectively.
Keywords
Article Details
References
- T. Ren, J. Wang, G. Li and Y. Li, Synthesis, Characterization and in vitro Antitumor Activity of Novel Schiff Bases Containing Pyrazole Group, Asian J. Chem., 26, 8309 (2014); https://doi.org/10.14233/ajchem.2014.16893
- S. Gama, F. Mendes, F. Marques, I.C. Santos, M.F. Carvalho, I. Correia, J.C. Pessoa, I. Santos and A. Paulo, Copper(II) Complexes with Tridentate Pyrazole-Based Ligands: Synthesis, Characterization, DNA Cleavage Activity and Cytotoxicity, J. Inorg. Biochem., 105, 637 (2011); https://doi.org/10.1016/j.jinorgbio.2011.01.013
- S. Abu Bakr, S.S. Abd El-Karim, M.M. Said and M.M. Youns, Synthesis and Anticancer Evaluation of Novel Isoxazole/Pyrazole Derivatives, Res. Chem. Intermed., 42, 1387 (2016); https://doi.org/10.1007/s11164-015-2091-5
- N.J.P. Subhashini, J. Amanaganti and P.A. Nagarjuna, Synthesis, Characterization and Biological Activity of (NE,NZ)-N1,N2-bis((1-Phenyl-3-aryl-1H-pyrazol-4-yl)methylene)benzene-1,2-diamines, J. Appl. Chem., 3, 2358 (2014).
- A.L. Iglesias, G. Aguirre, R. Somanathan and M. Parra-Hake, New Chiral Schiff Base-Cu(II) Complexes as Cyclopropanation Catalysts, Polyhedron, 23, 3051 (2004); https://doi.org/10.1016/j.poly.2004.09.007
- A.L. Iglesias and J.J. García, Homogeneous Hydrogenation of Fluoro-aromatic Imines with Ni compounds, evidence for h2-C=N Intermediate in the Catalytic Cycle, J. Mol. Catal. A Chem., 298, 51 (2009); https://doi.org/10.1016/j.molcata.2008.10.003
- A.L. Iglesias, M. Muñoz-Hernández and J.J. García, Fluoro Aromatic Imine Nickel(0) Complexes: Synthesis and Structural Studies, J. Organomet. Chem., 692, 3498 (2007); https://doi.org/10.1016/j.jorganchem.2007.04.026
- L.J. Villarreal-Gómez, I.E. Soria-Mercado, G. Guerra-Rivas and N.E. Ayala-Sánchez, Antibacterial and Anticancer Activity of Seaweeds and Bacteria Associated with their Surface, Rev. Biol. Mar. Oceanogr., 45, 267 (2010); https://doi.org/10.4067/S0718-19572010000200008
- V.C. Gibson, C. Redshaw and G.A. Solan, Bis(imino)pyridines: Surprisingly Reactive Ligands and a Gateway to New Families of Catalysts, Chem. Rev., 107, 1745 (2007); https://doi.org/10.1021/cr068437y
- S.C. Bart, E. Lobkovsky, E. Bill, K. Wieghardt and P.J. Chirik, Neutral-Ligand Complexes of Bis(imino)pyridine Iron: Synthesis, Structure, and Spectroscopy, Inorg. Chem., 46, 7055 (2007); https://doi.org/10.1021/ic700869h
- J.R. Zgoda and J.R. Porter, A Convenient Microdilution Method for Screening Natural Products Against Bacteria and Fungi, Pharm. Biol., 39, 221 (2001); https://doi.org/10.1076/phbi.39.3.221.5934
- K. Sztanke, A. Maziarka, A. Osinka and M. Sztanke, Aninsight into Synthetic Schiff Bases Revealing Antiproliferative Activities in vitro, Bioorg. Med. Chem., 21, 3648 (2013); https://doi.org/10.1016/j.bmc.2013.04.037
- C.M. da Silva, D.L. da Silva, L.V. Modolo, R.B. Alves, M.A. de Resende, C.V.B. Martins and Â. de Fátima, Schiff bases: A Short Review of their Antimicrobial Activities, J. Adv. Res., 2, 1 (2011); https://doi.org/10.1016/j.jare.2010.05.004
- P. Panneerselvam, M.G. Priya, N.R. Kumar and G. Saravanan, Synthesis and Pharmacological Evaluation of Schiff Bases of 4-(2-Aminophenyl)-morpholines, Indian J. Pharm. Sci., 71, 428 (2009); https://doi.org/10.4103/0250-474X.57292
- M.A. Neelakantan, M. Esakkiammal, S.S. Mariappan, J. Dharmaraja and T. Jeyakumar, Synthesis, Characterization and Biocidal Activities of Some Schiff Base Metal Complexes, Indian J. Pharm. Sci., 72, 216 (2010); https://doi.org/10.4103/0250-474X.65015
- A.W. Bauer, W.M.M. Kirby, J.C. Sherris and M. Turck, Antibiotic Susceptibility Testing by a Standardized Single Disk Method, Am. J. Clin. Pathol., 45, 493 (1966); https://doi.org/10.1093/ajcp/45.4_ts.493
- E.I. Nweze, P.K. Mukherjee and M.A. Ghannoum, Agar-Based Disk Diffusion Assay for Susceptibility Testing of Dermatophytes, J. Clin. Microbiol., 48, 3750 (2010); https://doi.org/10.1128/JCM.01357-10
References
T. Ren, J. Wang, G. Li and Y. Li, Synthesis, Characterization and in vitro Antitumor Activity of Novel Schiff Bases Containing Pyrazole Group, Asian J. Chem., 26, 8309 (2014); https://doi.org/10.14233/ajchem.2014.16893
S. Gama, F. Mendes, F. Marques, I.C. Santos, M.F. Carvalho, I. Correia, J.C. Pessoa, I. Santos and A. Paulo, Copper(II) Complexes with Tridentate Pyrazole-Based Ligands: Synthesis, Characterization, DNA Cleavage Activity and Cytotoxicity, J. Inorg. Biochem., 105, 637 (2011); https://doi.org/10.1016/j.jinorgbio.2011.01.013
S. Abu Bakr, S.S. Abd El-Karim, M.M. Said and M.M. Youns, Synthesis and Anticancer Evaluation of Novel Isoxazole/Pyrazole Derivatives, Res. Chem. Intermed., 42, 1387 (2016); https://doi.org/10.1007/s11164-015-2091-5
N.J.P. Subhashini, J. Amanaganti and P.A. Nagarjuna, Synthesis, Characterization and Biological Activity of (NE,NZ)-N1,N2-bis((1-Phenyl-3-aryl-1H-pyrazol-4-yl)methylene)benzene-1,2-diamines, J. Appl. Chem., 3, 2358 (2014).
A.L. Iglesias, G. Aguirre, R. Somanathan and M. Parra-Hake, New Chiral Schiff Base-Cu(II) Complexes as Cyclopropanation Catalysts, Polyhedron, 23, 3051 (2004); https://doi.org/10.1016/j.poly.2004.09.007
A.L. Iglesias and J.J. García, Homogeneous Hydrogenation of Fluoro-aromatic Imines with Ni compounds, evidence for h2-C=N Intermediate in the Catalytic Cycle, J. Mol. Catal. A Chem., 298, 51 (2009); https://doi.org/10.1016/j.molcata.2008.10.003
A.L. Iglesias, M. Muñoz-Hernández and J.J. García, Fluoro Aromatic Imine Nickel(0) Complexes: Synthesis and Structural Studies, J. Organomet. Chem., 692, 3498 (2007); https://doi.org/10.1016/j.jorganchem.2007.04.026
L.J. Villarreal-Gómez, I.E. Soria-Mercado, G. Guerra-Rivas and N.E. Ayala-Sánchez, Antibacterial and Anticancer Activity of Seaweeds and Bacteria Associated with their Surface, Rev. Biol. Mar. Oceanogr., 45, 267 (2010); https://doi.org/10.4067/S0718-19572010000200008
V.C. Gibson, C. Redshaw and G.A. Solan, Bis(imino)pyridines: Surprisingly Reactive Ligands and a Gateway to New Families of Catalysts, Chem. Rev., 107, 1745 (2007); https://doi.org/10.1021/cr068437y
S.C. Bart, E. Lobkovsky, E. Bill, K. Wieghardt and P.J. Chirik, Neutral-Ligand Complexes of Bis(imino)pyridine Iron: Synthesis, Structure, and Spectroscopy, Inorg. Chem., 46, 7055 (2007); https://doi.org/10.1021/ic700869h
J.R. Zgoda and J.R. Porter, A Convenient Microdilution Method for Screening Natural Products Against Bacteria and Fungi, Pharm. Biol., 39, 221 (2001); https://doi.org/10.1076/phbi.39.3.221.5934
K. Sztanke, A. Maziarka, A. Osinka and M. Sztanke, Aninsight into Synthetic Schiff Bases Revealing Antiproliferative Activities in vitro, Bioorg. Med. Chem., 21, 3648 (2013); https://doi.org/10.1016/j.bmc.2013.04.037
C.M. da Silva, D.L. da Silva, L.V. Modolo, R.B. Alves, M.A. de Resende, C.V.B. Martins and Â. de Fátima, Schiff bases: A Short Review of their Antimicrobial Activities, J. Adv. Res., 2, 1 (2011); https://doi.org/10.1016/j.jare.2010.05.004
P. Panneerselvam, M.G. Priya, N.R. Kumar and G. Saravanan, Synthesis and Pharmacological Evaluation of Schiff Bases of 4-(2-Aminophenyl)-morpholines, Indian J. Pharm. Sci., 71, 428 (2009); https://doi.org/10.4103/0250-474X.57292
M.A. Neelakantan, M. Esakkiammal, S.S. Mariappan, J. Dharmaraja and T. Jeyakumar, Synthesis, Characterization and Biocidal Activities of Some Schiff Base Metal Complexes, Indian J. Pharm. Sci., 72, 216 (2010); https://doi.org/10.4103/0250-474X.65015
A.W. Bauer, W.M.M. Kirby, J.C. Sherris and M. Turck, Antibiotic Susceptibility Testing by a Standardized Single Disk Method, Am. J. Clin. Pathol., 45, 493 (1966); https://doi.org/10.1093/ajcp/45.4_ts.493
E.I. Nweze, P.K. Mukherjee and M.A. Ghannoum, Agar-Based Disk Diffusion Assay for Susceptibility Testing of Dermatophytes, J. Clin. Microbiol., 48, 3750 (2010); https://doi.org/10.1128/JCM.01357-10