Synthesis and Biological Activities of Azalamellarins

The synthesis of azalamellarins, a new series of lactam analogues of biologically active lamellarins, was achieved using Cu^I‐mediated and microwave‐assisted C? N_amide bond formation. Seventeen azalamellarins, including N‐allylazalamellarins and N‐propylazalamellarins χ‐D, L ‐N, and J‐dehydro J, were synthesized and evaluated for their cytotoxicity against the cancer cell lines HuCCA‐1, A‐549, HepG2, and MOLT‐3. The results showed that certain azalamellarins exhibited good activities in the micromolar IC₅₀ value range (IC₅₀=the drug concentration that causes 50 % of cell‐growth inhibition after 72 h of continuous exposure to the test molecule), comparable to their parent lamellarin analogue.     

Synthesis of unsymmetrical benzil licoagrodione

A synthesis of unsymmetrical 1,2-diarylethane-1,2-dione is reported involving the intramolecular cyclization of anionic benzylic ester of the aryl benzyl ether followed by oxidation employing dioxirane. With the use of microwave irradiation, licoagrodione was prepared from Claisen rearrangement of the corresponding allyl phenyl ether 1,2-diketone readily available from the Lindlar's reduction of the corresponding alkyne derivative. Subsequent removal of protecting groups then furnished the desired product.