Synthesis of alkyl substituted α,β unsaturated γ lactones as potential antitumor agents

Article abstract of DOI:10.1021/jm00254a012

A series of alkyl substituted di and monolactones including (E,E) 3,3 (alkanediylidene)bis[dihydro 2(3H) furanones] and the monolactones was synthesized by reaction of α (triphenylphosphoranylidene) γ butyrolactone with appropriate aldehydes. The reaction of this ylide with formaldehyde gave α methylene γ butyrolactone. These compounds were tested for antitumor activity as part of a study to determine the influence of β substituents and distance between alkylating sites on the antitumor activity of α,β unsaturated lactones. The testing was carried out in standard National Cancer Institute screens and the compounds possessed ED₅₀ values of 16 to 110 μg/ml against cells derived from human carcinoma of the nasopharynx (KB) and were inactive against L1210 lymphoid leukemia in the mouse.