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  • Title: Synthesis and antitumor activity of simple vinyl and alpha-methylene-gamma-butyrolactone sulfonate esters and silyl enol ethers.
    Author: Stang PJ, Treptow WL.
    Journal: J Med Chem; 1981 Apr; 24(4):468-72. PubMed ID: 6267282.
    Abstract:
    A number of simple silyl enol ethers and vinyl trifluoromethanesulfonates, a relatively new class of organic compounds capable of undergoing alkylation by a nucleophilic addition-elimination process, were evaluated in the P388 lymphocytic leukemia system. No activity (ILS = 8-22%) was observed in the simple vinyl derivatives. Some activity (ILS = 20-42%) was observed for a series of siloxy and sulfonate (CH3SO2 and CF3SO3) functionalized alpha-methylene lactone systems. The enhanced activity of the functionalized systems over the parent methylene lactone is ascribed to a possible irreversible alkylation by cellular nucleophiles via a nucleophilic addition-elimination process.
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