Biological potential of thiazolidinedione derivatives of synthetic origin

Abstract

Thiazolidinediones are sulfur containing pentacyclic compounds that are widely found throughout nature in various forms. Thiazolidinedione nucleus is present in numerous biological compounds, e.g., anti-malarial, antimicrobial, anti-mycobacterium, anticonvulsant, antiviral, anticancer, anti-inflammatory, antioxidant, anti-HIV (human immunodeficiency virus) and antitubercular agent. However, owing to the swift development of new molecules containing this nucleus, many research reports have been generated in a brief span of time. Therefore seems to be a requirement to collect recent information in order to understand the current status of the thiazolidinedione nucleus in medicinal chemistry research, focusing in particular on the numerous attempts to synthesize and investigate new structural prototypes with more effective antidiabetic, antimicrobial, antioxidant, anti-inflammatory, anticancer and antitubercular activity.

Synthesis and Antibacterial Activity of New Thiazolidine-2,4-dione-Based Chlorophenylthiosemicarbazone Hybrids

“…The 4-thiazolidinone derivatives and their narrow group—thiazolidine-2,4-diones (TZDs)—are the object of special scientific studies. This is confirmed by numerous reviews [ 2 , 3 , 4 , 5 , 6 ]. This attention is due not only to the wide possibilities for chemical modification of these derivatives, but also to a diverse spectrum of pharmacological properties and affinity for various biological targets.…”

5‐(4‐Methoxybenzylidene)thiazolidine‐2,4‐dione‐derived VEGFR‐2 inhibitors: Design, synthesis, molecular docking, and anticancer evaluations

“…The synthetic strategy for the preparation of the target compounds ( 5–7 ) is depicted in Schemes 1 and 2. The synthesis was initiated by cyclocondensation of thiourea with chloroacetic acid to afford thiazolidine‐2,4‐dione ( 1 ), [ 39,40 ] which underwent further condensation reaction with 4‐methoxybenzaldehyde to afford 5‐(4‐methoxybenzylidene)‐thiazolidine‐2,4‐dione ( 2 ), which was heated with alcoholic potassium hydroxide to afford the corresponding potassium salt ( 3 ). On the contrary, chloroacyl chloride was reacted with the appropriate aromatic amine to obtain the corresponding chloroamides ( 4a–g ).…”

“…Thiazolidine‐2,4‐dione ( 1 ), 5‐(4‐methoxybenzylidene)thiazolidine‐2,4‐dione ( 2 ), the corresponding potassium salt ( 3 ), N ‐aryl‐2‐chloroacetamide derivatives, 4a–g , and 4‐(2‐chloroacetamido)‐ N ‐substitutedbenzamide derivatives, 6a–f , were obtained according to the reported procedures. [ 39,40,51–55 ]…”

Synthesis of Novel 4-Thiazolidinone and Bis-Thiazalidin-4-One Derivatives Derived from 4-Amino-Antipyrine and Evaluated as Inhibition of Purine Metabolism Enzymes by Bacteria

“…The Schiff's base of 4-amino-antipyrine is a group of systems showed a wide range of biological activities having the azomethine (-N=CH-) active pharmacophore, which plays major roles in their bio-active properties [10]. Also, the presence of cyclic (NCS-C=O) group in thiazolidin-4-ones often enhances those biological and pharmacological properties [12] [13] [14] [15]. Similarly, condensation of 4-aminoantipyrine (1) with selective halogenated aromatic aldehydes and/or heteroaldehydes in refluxing EtOH, yielded the Schiff's base 2a-f (Scheme 1).…”