Synthesis and Antibacterial Activity of Analogs of 5-Arylidene-3-(4-methylcoumarin-7-yloxyacetylamino)-2-thioxo-1,3-thiazoli-din-4-one

Abstract

Abstract:In an effort to develop new antimicrobial agents, 3-(4-methylcoumarin-7-yloxyacetylamino)-2-thioxo-1,3-thiazolidin-4-one (4) was synthesized by reaction of thiocarbonylbisthioglycolic acid with ethyl (4-methyl-2-oxo-2H-chromen-7-yloxy)acetohydrazide (3), which was prepared in turn from 7-hydroxy-4-methylcoumarin (1). The condensation of compound 4 with different aromatic aldehydes afforded a series of 5-(arylidene)-3-(4-methylcoumarin-7-yloxyacetyl-amino)-2-thioxo-1,3-thiozolidin-4-one analogs 5a-h. The structures of these synthetic compounds were elucidated on the basis of IR, 1 H-NMR and 13 C-NMR spectral data and ESI-MS spectrometric analysis. Compounds 5a-h were examined for their antibacterial activity against several strains of Gram-positive and Gram-negative bacteria.

Design, Synthesis and Antibacterial Evaluation of Some New 2-Phenyl-quinoline-4-carboxylic Acid Derivatives

“…Compound 4b was reacted with 3-dimethyl aminopropyl amine according to GP2 to give the desired product 5b 6 The in vitro antibacterial activities of newly-synthesized Compounds 5a 1 -5a 7 and 5b 1 -5b 6 were evaluated for their antibacterial activities against S. aureus (ATCC29213), B. subtilis (ATCC6633), E. coli (ATCC25922), P. aeruginosa (ATCC9027) and MRSA (ATCC43300) bacterial strains by the agar diffusion method [36]. Fifteen to twenty milliliters of agar media were poured into each petri dish.…”

“…Firstly, the newly-synthesized Compounds 5a 1 -5a 7 , 5b 1 -5b 6 were screened for their in vitro antibacterial activities by the agar diffusion method against a variety of different strains [35][36][37], including Staphylococcus aureus (S. aureus), Bacillus subtilis (B. subtilis), Escherichia coli (E. coli), Pseudomonas aeruginosa (P. aeruginosa) and one strain of methicillin-resistant Staphylococcus aureus (MRSA) bacteria. Their activities were compared to that of Compound 1 and the known antibacterial agents ampicillin and gentamycin.…”

“…Firstly, the newly-synthesized Compounds 5a1-5a7, 5b1-5b6 were screened for their in vitro antibacterial activities by the agar diffusion method against a variety of different strains [35][36][37] In order to obtain the amine functionality, the conventional method for the reduction of the nitro group was attempted by using 80% hydrazine hydrate in the presence of 10% Pd/C and isopropanol as a solvent under reflux, which furnished amino-substituted Compound 3 in a 92% yield [34]. The advantage of this reaction was that product isolation could be facilitated without purification using chromatography.…”

Synthesis and Antibacterial Activity of Some Derivatives of 2-Methylbenzimidazole Containing 1,3,4-Oxadiazole or 1,2,4-Triazole Heterocycle

“…In view of these observations, some new compounds (2-methylbenzimidazole derivatives bearing 1,3,4-oxadiazole or 1,2,4-triazole heterocycle) have been synthesized. Their antibacterial and antifungal potential were also evaluated as a continuation of our research on antimicrobial compounds [17].…”

Synthesis of New Heterocyclic Nitrogen System Bearing Thiazolopyrazole Moiety as New Biocidal Agents

“…The new compounds used at different concentrations (0.1 and 0.2 %) and the examined for antibacterial activity according to the reported method [11] (a mixture of meat extract, 5.0 g; peptone, 5.0 g; NaCl, 5.0 g and distilled water, 1000 mL). Streptomycin and tetracycline were used as controls for Grampositive and Gram-negative bacteria, respectively.…”