Synthesis and evaluation of antioxidant activity of some new benzylidene-thiazolidine-xanthine derivatives.

UNLABELLED The International Diabetes Federation reported that 246 million adults worldwide had diabetes mellitus and the prevalence of this syndrome was expected to increase continuously. AIM To design new compound with potential antidiabetic and antioxidant activity. MATERIAL AND METHODS New benzylidene-thiazolidine derivatives (BT2a-2e) were obtained by condensation of xanthine-thiazolidine-4-one (TZ-4-one) with aromatic aldehydes. The synthesized compounds were characterized by spectral method (IR, 1H-NMR, 13C-NMR) and their antioxidant potential has been also evaluated. RESULTS The synthesized compounds have important antioxidant effects as compared to xanthine-thiazolidine derivatives. The most active compounds were those obtained by condensation with 4-dimethylaminobenzaldehyde (BT2c) and 4-nitro-benzaldehyde (BT2e). CONCLUSIONS The chemical modulations performed on the structure of TZD-4-one have a good influence on their antioxidant potential.

[1]  M. Carvajal,et al.  Synthesis and DPPH Radical Scavenging Activity of Prenylated Phenol Derivatives , 2012, Molecules.

[2]  R. F. Melo-Silveira,et al.  Molecular Sciences in Vitro Antioxidant, Anticoagulant and Antimicrobial Activity and in Inhibition of Cancer Cell Proliferation by Xylan Extracted from Corn Cobs , 2022 .

[3]  K. E. Malterud,et al.  Chemical, Antioxidant and Antimicrobial Investigations of Pinus cembra L. Bark and Needles , 2011, Molecules.

[4]  Z. Chohan Metal-based antibacterial and antifungal sulfonamides: synthesis, characterization, and biological properties , 2009 .

[5]  N. Pai,et al.  Synthesis and biological activity of N-substituted-3-chloro-2-azetidinones. , 2007, Molecules.

[6]  C. S. Rajput,et al.  Synthesis of 3-[4'-(p-chlorophenyl)-thiazol-2'-yl]-2-[(substituted azetidinone/thiazolidinone)-aminomethyl]-6-bromoquinazolin-4-ones as anti-inflammatory agent. , 2007, Bioorganic & medicinal chemistry.

[7]  B. Kalluraya,et al.  The synthesis and antimicrobial study of some azetidinone derivatives with the para-anisidine moiety , 2007 .

[8]  J. Ellena,et al.  Copper complexes with heterocyclic sulfonamides: synthesis, spectroscopic characterization, microbiological and SOD-like activities: crystal structure of [Cu(sulfisoxazole)2(H2O)4] . 2H2O. , 2006, Journal of inorganic biochemistry.

[9]  C. Supuran,et al.  Carbonic anhydrase inhibitors: sulfonamides incorporating furan-, thiophene- and pyrrole-carboxamido groups possess strong topical intraocular pressure lowering properties as aqueous suspensions. , 2000, Bioorganic & medicinal chemistry.