SYNTHESIS, ANTIBACTERIAL AND ANTIOXIDANT EVALUATION OF 4-SUBSTITUTED 1-(4-METHOXYPHENYL)PYRROLIDIN-2-ONES

4-Substituted 1-(4-methoxyphenyl)pyrrolidin-2-ones containing azole, diazole, oxadiazole, thiadiazole, and triazole fragments have been synthesized, and the characterization of the obtained products is presented. The study compounds have been analyzed for antioxidant and antibacterial activities. Two types of hetero systems – 5-thioxo-4,5-dihydro-1,3,4-oxadiazole and [1,2,4]triazolo[3,4- b ][1,3,4]thiadiazine – showed a moderate activity against Rhizobium radiobacter , Xanthomonas campestris , and Escherichia coli microorganisms. Some compounds were tested for their antioxidant activity. DOI: http://dx.doi.org/10.5755/j01.ct.65.1.8881

[1]  A. K. Shrivastava,et al.  Synthesis of 5-arylidine amino-1,3,4-thiadiazol-2-[(N-substituted benzyol)]sulphonamides endowed with potent antioxidants and anticancer activity induces growth inhibition in HEK293, BT474 and NCI-H226 cells , 2013, Medicinal Chemistry Research.

[2]  P. Venskutonis,et al.  Synthesis and Biological Activity of 3-[Phenyl(1,3-thiazol-2-yl)-amino]propanoic Acids and Their Derivatives , 2013, Molecules.

[3]  A. Malm,et al.  Synthesis and antimicrobial evaluation of some novel 1,2,4-triazole and 1,3,4-thiadiazole derivatives , 2012, Medicinal Chemistry Research.

[4]  I. Jonuškienė,et al.  The synthesis of azole derivatives from 3-[(4-methylphenyl)amino]propanehydrazide and its N′-phenylcarbamoyl derivatives, and their antibacterial activity , 2012, Monatshefte für Chemie - Chemical Monthly.

[5]  M. Stasevych,et al.  Reactions of 5-oxo-1-phenylpyrrolidine-3-carbohydrazides with 1,4-naphthoquinone derivatives and the properties of the obtained products , 2011 .

[6]  Sanjay Kumar,et al.  Synthesis and anti-microbial evaluation of some novel 1,2,4-triazole derivatives. , 2011, Acta poloniae pharmaceutica.

[7]  M. Stasevych,et al.  Synthesis and Biological Activity of Mono- and Disubstituted 1,2,4-Triazole Derivatives. , 2010 .

[8]  N. Karami,et al.  Antimicrobial activity of topical skin pharmaceuticals - an in vitro study. , 2010, Acta dermato-venereologica.

[9]  R. Vaickelionienė,et al.  Synthesis and properties of 1-(3-(fluoromethyl and trifluoromethyl)phenyl)-5-oxopyrrolidine-3-carboxylic acid derivatives , 2009 .

[10]  R. Vaickelionienė,et al.  Synthesis of substituted 1,3,4-oxadiazole derivatives , 2009 .

[11]  Žaneta Maželienė,et al.  Synthesis of Azole Derivatives from 3-Phenylaminopropanohydrazide and Evaluation of Their Antimicrobial Efficacy. , 2009 .

[12]  H. Walter New Carboxylic Acid Amides of the Pyrrole Series: Synthetic Routes and Biological Aspects , 2008 .

[13]  V. Mickevičius,et al.  Synthesis and structural investigation of some 1,4-disubstituted-2-pyrrolidinones , 2005 .

[14]  T. I. Apak,et al.  Synthesis of new triazolyl-N,N-Dialkyldithiocarbamates as antifungal agents , 2005, Archives of pharmacal research.

[15]  R. Mabagala,et al.  Identification and Characterisation of Xanthomonas campestris pv. campestris Strains from Tanzania by Pathogenicity Tests, Biolog, rep-PCR and Fatty Acid Methyl Ester Analysis , 2003, European Journal of Plant Pathology.

[16]  P. Hsueh,et al.  Clinical and microbiological characteristics of Rhizobium radiobacter infections. , 2004, Clinical infectious diseases : an official publication of the Infectious Diseases Society of America.

[17]  U. Bonas,et al.  Genomic approaches in Xanthomonas campestris pv. vesicatoria allow fishing for virulence genes. , 2003, Journal of biotechnology.

[18]  Yanli Wang,et al.  Syntheses and insecticidal activities of novel 2,5-disubstituted 1,3,4-oxadiazoles , 2003 .

[19]  B. Poojary,et al.  Synthesis characterization and anticancer activity studies on some Mannich bases derived from 1,2,4-triazoles. , 2003, European journal of medicinal chemistry.

[20]  A. Atalla,et al.  Novel synthesis and antifungal activity of pyrrole and pyrrolo[2,3-d]pyrimidine derivatives containing sulfonamido moieties. , 2002, Farmaco.

[21]  H. Hof Critical Annotations to the Use of Azole Antifungals for Plant Protection , 2001, Antimicrobial Agents and Chemotherapy.

[22]  T. El‐Emary,et al.  New pyrazolo[3,4-b]pyrazines: synthesis and biological activity. , 2000, Die Pharmazie.

[23]  J. Kane,et al.  2,4-Dihydro-3H-1,2,4-triazole-3-thiones as potential antidepressant agents. , 1988, Journal of medicinal chemistry.