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The research about α-methylene-γ-lactams is scarce; however, their synthesis has emerged in recent years mainly because they are isosters of α-methylene-γ-lactones. This last kind of compound is structurally most common in some natural products’ nuclei, like sesquiterpene lactones that show biological activity such as anti-inflammatory, anticancer, antibacterial, etc., effects. In this work, seven α-methylene-γ-lactams were evaluated by their inflammation and α-glucosidase inhibition. Thus, compounds <i>3-methylene-4-phenylpyrrolidin-2-one</i> (<b>1</b>), <i>3-methylene-4-(p-tolyl)pyrrolidin-2-one</i> (<b>2</b>), <i>4-(4-chlorophenyl)-3-methylenepyrrolidin-2-one</i> (<b>3</b>), <i>4-(2-chlorophenyl)-3-methylenepyrrolidin-2-one</i> (<b>4</b>), <i>5-ethyl-3-methylene-4-phenylpyrrolidin-2-one</i> (<b>5</b>), <i>5-ethyl-3-methylene-4-(p-tolyl)pyrrolidin-2-one</i> (<b>6</b>) and <i>4-(4-chlorophenyl)-5-ethyl-3-methylenepyrrolidin-2-one</i> (<b><i>7</i></b>) were evaluated via in vitro α-glucosidase assay at 1 mM concentration. From this analysis, <b>7</b> exerts the best inhibitory effect on α-glucosidase compared with the vehicle, but it shows a low potency compared with the reference drug at the same dose. On the other side, inflammation edema was induced using TPA (12-<i>O</i>-tetradecanoylphorbol 13-acetate) on mouse ears; compounds <b>1</b>–<b>7</b> were tested at 10 µg/ear dose. As a result, <b>1</b>, <b>3</b>, and <b>5</b> show a better inhibition than indomethacin, at the same doses. This is a preliminary report about the biological activity of these new α-methylene-γ-lactams.