Z)-7 -SulfonyI-3-hexen-I,5-diyne containing molecules are stable at room temperature and isomerized to eneyne-allene-sulfones under alkaline conditions. These eneyne-allene-sulfones were not isolable, spontaneously cyclized to form biradical intermediates under mild conditions, and exhibited good DNA-cleaving and human tumor cell line growth inhibition properties. Further studies indicated that compounds bearing on aromatic ring at C(3) and C(4), such as 25, proved to be more active against those tumor cell lines. Removal of acetylene unit at C(l) and e(2), made the resulting compound less active. A related compound, (Z,Z)-12-(2-tetrahydropyranyl)oxy-I-phenylsulfonyldodeca-4,8-diene-2,6, lO-triyne (37), was synthesized. Upon treatment of triethylamine at refluxing benzene, this compound undergoes double cycloaromatization to form a naphalenc adduct, which possesses excellent DNA-cleaving activity. Scheme Ito [-~]

A series of molecules containing monopropargyl sulfone or 1, 2‐bis‐propargyl sulfone were synthesized. The cytotoxicity of these compounds against human carcinoma cells was also examined. This study indicated that the formation of a biradical intermediate is important to the potency of cytotoxicity.

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