The coumarin (benzopyran-2-one, or chromen-2-one) ring system, present in many natural products, displays diverse pharmacological properties. It has attracted the attention of chemists and medicinal chemists for decades. Many molecules based on the coumarin ring system have been described utilizing innovative synthetic methods. These synthetic routes have led to interesting analogues of coumarins which possess pharmacological activities like anti-HIV, antimicrobial, antiinflammatory, anticancer, anti-TB, anticonvulsant and MAO inhibitory properties. Details of these studies, correlating structure with biological activity are described in this review.

Controlled monosulphenylation a t carbon adjacent to electron-withdrawing groups can be achieved by the controlled reduction of readily available bis-sulphenylated products.

BackgroundThiazolidinediones (TZDs), also called glitazones, are five-membered carbon ring molecules commonly used for the management of insulin resistance and type 2 diabetes. Recently, many prospective studies have also documented the impact of these compounds as anti-proliferative agents, though several negative side effects such as hepatotoxicity, water retention and cardiac issues have been reported. In this work, we synthesized twenty-six new TZD analogues where the thiazolidinone moiety is directly connected to an N-heterocyclic ring in order to lower their toxic effects.MethodsBy adopting a widely applicable synthetic method, twenty-six TZD derivatives were synthesized and tested for their antiproliferative activity in MTT and Wound healing assays with PC3 (prostate cancer) and MCF-7 (breast cancer) cells.ResultsThree compounds, out of twenty-six, significantly decreased cellular viability and migration, and these effects were even more pronounced when compared with rosiglitazone, a well-known member of the TZD class of antidiabetic agents. As revealed by Western blot analysis, part of this antiproliferative effect was supported by apoptosis studies evaluating BCL-xL and C-PARP protein expression.ConclusionOur data highlight the promising potential of these TZD derivatives as anti-proliferative agents for the treatment of prostate and breast cancer.

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An efficient, cost-effective and large-scale synthesis of ezetimibe 1, an antihypercholesterolemia drug, is described. Chiral oxazolidinone chemistry was used to fix the required stereochemistry of the β-lactam ring, and the chiral oxazaborolidine chemistry was used to fix the hydroxyl group stereochemistry. The synthesis significantly lowers the cost and provides easy access to ezetimibe on large scale.