Synthesis of C(10)-halogenated prostaglandins

The synthesis of halogenated prostaglandins at position C(10), starting from prostaglandin A₂, has been accomplished, as well as an efficient regioselective hydroxylation of the upper chain of the prostanoid structure. Evaluation of the inhibitory effects on the proliferation of the K-562 cell line in vitro is presented. When the prostaglandin was modified in the upper chain, the antimitotic activity for bromo derivatives 4b,c and iodo derivative 5b had shown substantial improvements in their activities according to their ID₅₀ values (28, 25, and 22 μg/mL, respectively). Attention is called to the significance of chloro derivative 3a in terms of its high potency, determined by its ID₅₀ value (0.06 μg/mL.).