Synthesis and characterization of polar functional group substituted mono- and bis-(o-carboranyl)-1,3,5-triazine derivatives

Synthesis, structural characterization, and biological activity studies of o-carborane-substituted 1,3,5-triazines (9-12) containing polar functional groups such as methoxyethyl and t-butoxycarbonylmethyl amine units are described. De-methylation of di(methoxyethyl)amine functionalized triazines 9 and 10 resulted in the production of di(hydroxyethyl)amine derivatives 13 and 14. NNIR (H-1 and C-13) and X-ray crystallographic studies confirmed the structures derived from the sequential o-carborane substitution on the 1,3,5-triazine core. Preliminary in vitro studies revealed that compounds 9, 10, 13, and 14, despite their low cytotoxicity, accumulated at high levels in B-16 melanoma cells. (c) 2007 Elsevier Ltd. All rights reserved.