Synthesis, characterization and antimicrobial evaluation of imidazolyl thiazolidinedione derivatives

Abstract

Two series of 2,4 thiazolidinedione derivatives (T 1 -T 4 ) and (T 5 -T 8 ) containing substituted imidazoles and one series of 5-substituted 2,4-thiazolidinedione derivatives (T 9 -T 12 ) were designed and synthesized. The chemical structures of all the three series of 2,4 thiazolidinedione derivatives have been elucidated by spectral studies (IR, 1 H NMR, 13 C NMR and Mass spectra). The compounds were screened for their anti-bacterial activity against Staphylococcus aureus ATCC-9144, Staphylococcus epidermidis ATCC-155, Escherichia coli ATCC-25922, Pseudomonas aeruginosa ATCC-2853 bacterial species and antifungal activity against Aspergillus niger ATCC-9029, Aspergillus fumigatus ATCC-46645 by the paper disc diffusion technique. The minimum inhibitory concentrations (MICs) of the compounds were also determined by the agar streak dilution method. Among the synthesized compounds methyl-2-(4-((3-(2-methoxy-2-oxoethyl)-2,4-dioxothiazolidine-5-ylidene) methyl)-1H-imidazol-1-yl) acetate (T 2 ), methyl-2-(5-((1-(2-(4-fluorophenylthio)ethyl)-1H-imidazol-4-yl)methylene)-2,4-dioxo thiazolidin-3-yl)acetate (T 4 ) and methyl-2-(2-((3-(2-methoxy-2-oxoethyl)-2,4-dioxothiazolidine-5-ylidene) methyl)-1H-imidazol-1-yl) acetate (T 8 ) were found to possess moderately potent antimicrobial activity with MIC of 1.9, 1.4, 1.6, 0.56, 8.8, 2.3 lg/ml (T 2 ), 3.8, 2.2, 1.6, 2.8, 7.9, 1.7 lg/ml (T 4 ) and 2.7, 3.39, 3.2, 1.4, 8.2, 3.4 lg/ml (T 8 ) against the above mentioned respective strains. All other compounds had shown mild to moderate antibacterial and antifungal activities. ª 2014 Production and hosting by Elsevier B.V. on behalf of King Saud University.

Design, synthesis, in silico studies and biological evaluation of 5-((E)-4-((E)-(substituted aryl/alkyl)methyl)benzylidene)thiazolidine-2,4-dione derivatives

“…The synthesis of TZD derivatives (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20) were accomplished using the synthetic route depicted in Scheme 1. At first, 2-chloroacetic acid was treated with thiourea in conc.…”

“…Further, the reaction of (I) with terephthalaldehyde yielded 4-((2,4-dioxothiazolidin-5-ylidene) methyl) benzaldehyde (II). Intermediate-II on further treatment with substituted anilines/amines yielded final 5-((E)-4-((E)-(substituted aryl/alkyl)methyl)benzylidene)thiazolidine-2,4-dione derivatives (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20). The physicochemical characterization and spectral analysis of the synthesized derivatives are given in Table 1.The molecular structures of the synthesized derivatives (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20) were established using elemental analysis and spectral studies [FT-IR (KBr, cm -1 ), 1…”

“…To the solution of compound II (0.01 mol) in methanol (50 mL), different substituted amines (0.01 mol) were added using catalytic amount of acetic acid (glacial) and refluxed for 4-18 h. The reaction mixture was then allowed to cool and finally recrystallized from methanol to give final compounds (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20).…”

Design, synthesis, in silico studies and biological evaluation of 5-((E)-4-((E)-(substituted aryl/alkyl)methyl)benzylidene)thiazolidine-2,4-dione derivatives

“…The synthesis of TZD derivatives (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20) were accomplished using the synthetic route depicted in Scheme 1. At first, 2-chloroacetic acid was treated with thiourea in conc.…”

Synthesis and Antimicrobial Activity of a New Series of Thiazolidine-2,4-diones Carboxamide and Amino Acid Derivatives

“…Accordingly, considerable attention has been devoted to thiazolidinedione derivatives (TZDs), both from a synthetic point of view and biological applications [1][2][3][4][5][6]. In this regard, TZDs have been used as the following: antibacterial and antifungal agents [7][8][9][10][11][12]; anti-inflammatory drugs [13][14][15][16]; aldose reductase inhibitors [17,18]; and anticancer [19][20][21][22][23][24][25], antiplasmodial inhibitors [26], and antidiabetic agents [27][28][29][30][31][32]. Consequently, TZDs…”