Synthesis, structure elucidation, and anti-inflammatory/anti-cancer/anti-bacterial activities of novel (Z)-3-adamantyl-1-aryl-prop/but-2-en-1-ones

A series of hitherto unreported (Z)-3-adamantyl-1-aryl-prop/but-2-en-1-ones (4a-j) were prepared from formylated/acetylated active proton compounds (2a-j) and 1-adamantanamine (3) under microwave irradiation in good to excellent yields. The structures of 4a-j have been unequivocally established with the help of spectral and analytical data. All the products were found to exist in Z form which was also supported by X-ray crystallographic studies. Compounds 4a-j were assessed for their biological activities by testing their anti-inflammatory, anti-cancer, and anti-bacterial properties. The compounds 4h and 4i showed highest anti-inflammatory properties, while the compounds 4a and 4g were found to be the most cytotoxic and may have anti-cancer properties. However, none of the compounds exhibited anti-bacterial activity.