Abstract
2,4‐Thiazolidinedione (TZD) is a privileged and highly utilised scaffold for the development of pharmaceutically active compounds. This sulfur‐containing heterocycle is a versatile pharmacophore that confers a diverse range of pharmacological activities. TZD has been shown to exhibit biological action towards a vast range of targets interesting to medicinal chemists. In this review, we attempt to provide insight into both the historical conventional and the use of novel methodologies to synthesise the TZD core framework. Further to this, synthetic procedures utilised to substitute the TZD molecule at the activated methylene C5 and N3 position are reviewed. Finally, research into developing clinical agents, which act as modulators of peroxisome proliferator‐activated receptors gamma (PPARγ), protein tyrosine phosphatase 1B (PTP1B) and aldose reductase 2 (ALR2), are discussed. These are the three most targeted receptors for the treatment of diabetes mellitus (DM).
Highlights
Introduction to TZDHeterocyclic systems are recognised to be of great importance due to their proven utility within the field of medicinal chemistry.[1]
Due to the diverse range of reactions that can be conducted on the TZD core framework it is unsurprising that substituted TZDs exhibit a vast range of pharmacological activities
The most common utilisation of TZD-containing structures has been in the treatment of diabetes mellitus (DM), which is recognised as a metabolic disorder often characterised by hyperglycaemia and related ailments caused due to a deficiency in insulin secretion
Summary
Heterocyclic systems are recognised to be of great importance due to their proven utility within the field of medicinal chemistry.[1] It has been estimated that more than 85 % of all chemical entities which evoke a biological reaction contain at least one heterocycle.[2] The incorporation of heterocycles into drug molecules allows for organic chemists to modulate pharmacokinetic and pharmacodynamic properties, by altering such parameters as lipophilicity, polarity, hydrogen bonding ability as well as toxicological profiles.[2] It is, unsurprising that organic chemists have become highly familiar with heterocycles featuring various ring sizes. Aside from its use within the sphere of organic and medicinal chemistry, TZD acts as an inhibitor for the corrosion of steels in acidic environments and is reported as a ‘brightener’ in the electroplating industry.[5]
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