Synthesis and antimicrobial activities of some new 5-((3-(aryl)-1-phenyl-1H-pyrazol-4-yl)methylene)-3-phenylthiazolidine-2,4-diones

Abstract

A series of nine new compounds of 5-((3-(aryl)-1-phenyl-1H-pyrazol-4-yl)methylene)-3-phenylthiazolidine-2,4-diones was synthesized by Knoevenagel condensation of various 3-(aryl)-1-phenyl-1H-pyrazole-4-carbaldehydes with 3-phenylthiazolidine-2,4-dione in ethanol in the presence of piperidine as a catalyst. The reaction afforded the desired products in good yields. All the nine compounds were screened for their in vitro antibacterial (Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa and Escherichia coli) and antifungal (Aspergillus niger and A. flavus) activity. Biological activities of these compounds were compared with those of commercially available antibiotics, ciprofloxacin and antifungal agent fluconazole. Two compounds 3e and 3i were found to be most effective against S. aureus and B. subtilis. Out of the nine compounds tested for antifungal activity, five, 3c-f and 3h showed more than 50% inhibition against the A. flavus, whereas the three compounds 3a, 3d and 3f showed more than 50% inhibition against A. niger.

Synthetic approaches, structure activity relationship and biological applications for pharmacologically attractive pyrazole/pyrazoline–thiazolidine-based hybrids

“…44) were investigated for their antimicrobial activity. The most effective pyrazole-thiazolidinones included the 4-Br-phenyl or thiophene fragments in molecules and showed 2e4 times higher efficiency (MIC ¼ 16e31 mg/mL) in comparison with other derivatives [80]. The moderate antimicrobial activity towards E. coli and S. aureus was identified for 3N-glycoside substituted 2-thioxo- 4-thiazolidinone derivatives 4.58 (Fig.…”

Synthesis, Characterization and Antimicrobial Activity of 1,2‐dihydroquinoxaline‐3‐yl‐3‐Substitutedphenyl‐1H‐pyrazole‐4‐Carbaldehyde

“…The prevalence of pyrazole cores in biologically active molecules has stimulated the need for elegant and efficient ways to make these heterocyclic lead. Pyrazole derivatives are found to possess wide spectrum of pharmacological properties such as antibacterial , antifungal , antimicrobial , antidiabetic , herbicidal , antitumor , anti‐anxiety , and as active pharmacophore in celecoxib (as COX‐2 inhibitor) and sildenafil citrate (as cGMP‐specific phosphodiesterase type 5 inhibitor), etc.…”

Synthesis, HIV-1 RT inhibitory, antibacterial, antifungal and binding mode studies of some novel N-substituted 5-benzylidine-2,4-thiazolidinediones

“…Structural modifications of thiazolidinediones at 3 rd and 5 th position have exhibited significant biological activities [ 31 ]. In view of the mentioned above facts, and based on in silico studies carried out on thiazolidine 2,4-diones as HIV-1- RT inhibitors [ 32 ], a novel series of 2,4-thiazolidinedione analogs have been designed based on the pharmacophoric model of NNRTIs 18 with the thiazolidinedione moiety attached to the propionamide moiety (−CH 2 -CH 2 -CO-NH-) constituting the “body (hydrophilic)” flanked by aryl rings (hydrophobic) linked to the 3rd and 5th position of the thiazolidinedione ring and to that of substituted aromatic amines as the “wings” to enhance the hydrophobicity of the molecules (Figure 1 ).…”