Direct synthesis of the arylboronic acid analogues of phenylglycine via microwave-assisted four-component Ugi reaction

A four-component Ugi reaction (Ugi-4CR) utilizing formylphenyl boronic acids under mild condition was developed for the synthesis of arylboronic acid analogs. The reactions were performed in methanol and accelerated by microwave irradiation, which makes this strategy suitable for constructing boronic-containing chemical libraries. Two of the synthesized analogs were found to have cytotoxic activity against HepG2, MDA-MB231, and A549 cancer cell lines, demonstrating the potential application of this approach in developing novel boron-containing pharmaceuticals.

87In this study, an Ugi four-component reaction (Ugi-4CR) utilizing unprotected boronic acid building blocks under mild condition is developed. The described reactions were performed in methanol and accelerated by employing microwave irradiation. This strategy allows the direct generation of boronic acid analogs without protection and deprotection operations of boronic acid moiety, making it suitable for the preparation of boron-containing chemical libraries. The synthesized boronic acid analogs were subsequently evaluated for their cytotoxic activity by the MTT assay. Two potential lead compounds were found to be cytotoxic against HepG2, MDA-MB231, and A549 cancer cell lines, demonstrating the potential application of this approach in developing novel boron-containing pharmaceuticals.