Synthesis of branched-chain apiosylpyrimidines and their inhibition of lymphocyte proliferation

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Abstract
Branched-chain nucleosides containing .beta.-D-apio-L-furanose were synthesized by condensation of the bis(trimethylsilyl) derivative of uracil (11), thymine (12), 5-bromouracil (13) and 5-iodouracil (14) with the protected 1-O-acetylapiose in the presence of a Friedel-Crafts catalyst. Compounds (11) and (12) showed immunosuppressive activity for rat T[thymus-derived]-lymphocytes stimulated to grow by phytohemagglutinin but exhibited no inhibitory activity against herpes simplex virus. Compounds 11-14 did not inhibit herpes simplex virus replication, while low inhibition was obtained with the 1 nucleoside containing D-apio-D-furanose, D-apio-D-furanosyladenine. Compounds (13), (14), bromouridine and iodouridine suppressed growth of human lymphoblasts significantly more than the nonhalogenated apiosylpyrimidines.

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