TAILIEUCHUNG - Aneja et al. Organic and Medicinal Chemistry Letters 2011, 1:15

Aneja et al. Organic and Medicinal Chemistry Letters 2011, 1:15 ORIGINAL Open Access Synthesis of new pyrazolyl-2, 4-thiazolidinediones as antibacterial and antifungal agents Deepak K Aneja1*, Poonam Lohan1, Sanjiv Arora1, Chetan Sharma2, Kamal R Aneja2 and Om Prakash3† Abstract Background: Thiazolidine-2, 4-diones (TZDs) have become a pharmacologically important class of heterocyclic compounds since their introduction in the form of glitazones into the clinical use for the treatment of type 2 diabetes. TZDs lower the plasma glucose levels by acting as ligands for gamma peroxisome proliferators-activated receptors. In addition, this class of heterocyclic compounds possesses various other biological activities such as antihyperglycemic, antimicrobial, anti-inflammatory, anticonvulsant, insecticidal,. | Aneja et al. Organic and Medicinal Chemistry Letters 2011 1 15 http content 1 1 15 o Organic and Medicinal Chemistry Letters a SpringerOpen Journal ORIGINAL Open Access Synthesis of new pyrazolyl-2 4-thiazolidinediones as antibacterial and antifungal agents 1 1 r- A 1 2 2 3 Deepak K Aneja Poonam Lohan Sanjiv Arora Chetan Sharma Kamal R Aneja and Om Prakash 1 Abstract Background Thiazolidine-2 4-diones TZDs have become a pharmacologically important class of heterocyclic compounds since their introduction in the form of glitazones into the clinical use for the treatment of type 2 diabetes. TZDs lower the plasma glucose levels by acting as ligands for gamma peroxisome proliferators-activated receptors. In addition this class of heterocyclic compounds possesses various other biological activities such as antihyperglycemic antimicrobial anti-inflammatory anticonvulsant insecticidal etc. TZDs are also known for lowering the blood pressure thereby reducing the chances of heart failure and micro-albuminuria in the patients with type 2 diabetes. Results We have described herein the synthesis of three series of compounds namely ethyl 2- Z -5- 3-aryl-1-phenyl-1H-pyrazol-4-yl methylene -2 4-dioxothiazolidin-3-yl acetates 4 methyl 2- Z -5- 3-aryl-1-phenyl-1H-pyrazol-4-yl methylene -2 4-dioxothiazolidin-3-yl acetates 5 and 2- Z -5- 3-aryl-1-phenyl-1H-pyrazol-4-yl methylene -2 4-dioxothiazolidin-3-yl acetic acids 6 . The compounds 4 and 5 were synthesized by Knoevenagel condensation between 3-aryl-1-phenyl-1H-pyrazole-4-carbaldehydes 1 and ethyl methyl 2- 2 4-dioxothiazolidin-3-yl acetates 3 2 in alcohol using piperidine as a catalyst. The resultant compounds 4 and 5 having ester functionality were subjected to acidic hydrolysis to obtain 6. All the new compounds were tested for their in vitro antibacterial and antifungal activity. Conclusions Knoevenagel condensation approach has offered an easy access to new compounds 4-6. Antimicrobial evaluation of the

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