Many biologically active compounds such as natural products and clinical drugs for cardiovascular, inflammatory diseases, diabetes and cancer have one or more constituent cyclopropyl rings. The Coumarin scaffold has been extensively studied for biological activity due to its wide-ranging biological profiles, including activity as anticancer, anti-inflammatory, antibacterial, antifungal, and anticoagulant agents. Despite the potential for increased biological activity, cyclopropanated derivatives of coumarins have not been extensively investigated. Michael-initiated ring closure (MIRC) reaction is one of the principle reactions to cyclopropanate α,β-unsaturated alkenes. In the current research, MIRC was employed as a single-step route for the synthesis of cyclopropylated coumarins. However, the formation of novel highly strained tricyclic ketals based around the coumarin ring template was also observed. Many derivatives have been synthesized based on various electron-donating/electron-withdrawing substitutions at 5, 6, 7 and 8-positions on the coumarin ring structure. Electron-withdrawing groups and alkyl electron-donating groups lead to the preferential formation of the tricyclic ketal. Electron-donating groups result in the formation of a mixture of products. Benzamide-containing coumarins predominantly afford the tricyclic ketal. The synthesized compounds have been found to have toxicity in breast and renal cancer cell lines.

Studies into the formation of cylopropylated coumarins

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