Synthesis and evaluation of furan, thiophene, and azole bis[(carbamoyloxy)methyl] derivatives as potential antineoplastic agents

Article abstract of DOI:10.1021/jm00378a006

A series of bis(hydroxymethyl)-substituted heterocycles were synthesized and converted to the corresponding bis(methylcarbamate) derivatives. The heterocyclic systems studied were based on 2-phenyl-3-methylfuran, 1-phenylpyrazole, 1-phenyl-5-methylpyrazole, 1-phenyl-5-methylthiopene, 1-phenyl-1,2,3-triazole, 3-phenylisoxazole, 3-phenylisothiazole, 2-phenylthiazole, and 2-phenyloxazole. None of the bis(carbamates) prepared was active against murine P388 lymphocytic leukemia. Pyrrole bis(carbamate), which exhibited antileukemic activity, also showed reactivity toward 4-(p-nitrobenzyl)pyridine while the inactive bis(carbamates) were unreactive in the 4-(p-nitrobenzyl)pyridine assay.