A Brief Review on the Development of Novel Potentially Active Azetidin-2-ones Against Cancer

Abstract

Azetidin-2-ones (β-lactams) and its derivatives are an important group of heterocyclic compounds that exhibit a wide range of pharmacological properties such as antibacterial, anticancer, anti-diabetic, anti-inflammatory and anticonvulsant. Efforts have been made over the years to develop novel congeners with superior biological activities and minimal potential for undesirable side effects. The present review aimed to highlight some recent discoveries (2013-2019) on the development of novel azetidin-2-one-based compounds as potential anticancer agents.

One-Pot Construction of Diverse β-Lactam Scaffolds via the Green Oxidation of Amines and Its Application to the Diastereoselective Synthesis of β-Amino Acids

“…β-Lactams are important heterocycles used in the synthesis of antibiotics like penicillins and carbacephems, as well as the anticancer drug, paclitaxel (Taxol), and their demand is ever increasing (Figure ). In addition, β-lactams are important synthetic intermediates because they can be hydrolyzed to the corresponding amino acid derivatives. − From the viewpoint of diversity, it is highly desirable to develop new synthetic methods for constructing β-lactam derivatives that cannot be synthesized by conventional methods. In particular, new synthetic methods that give β-lactam derivatives intended for drug discovery should allow a wide range of substitution patterns while maintaining excellent stereoselectivity …”

Copper-Catalyzed Enantioconvergent Radical C(sp3)–N Cross-Coupling to Access Chiral α-Amino-β-lactams

“…Chiral β-lactams, an important class of heterocyclic compounds, are present in a wide range of natural products and pharmaceutical molecules. − Among them, chiral α-amino-β-lactams with pronounced biological activities have attracted the interest of synthetic organic chemists. − Notable examples of these chiral α-amino-β-lactams have attractive antibacterial activities, such as penicilliums, nocardicins, and sulfazecin (Scheme A). As a result, a variety of synthetic strategies have been elegantly developed for the construction of chiral α-amino-β-lactams. ,− Among them, the most popular strategy is the asymmetric Staudinger [2 + 2] cycloaddition, which has been successfully applied to the synthesis of antibiotic precursors containing chiral α-amino-β-lactams, such as loracarbef and Gram-negative strains (Scheme B, left).…”