Synthesis and Structure of -Carboranyl Azide and Its "Click" Reactions.

Novel zwitter-ionic -carboranyl azide 9-N(CH)MeN--7,8-CBH was prepared by the reaction of 9-Cl(CH)MeN--7,8-CBH with NaN. The solid-state molecular structure of -carboranyl azide was determined by single-crystal X-ray diffraction. 9-N(CH)MeN--7,8-CBH was used for the copper(I)-catalyzed azide-alkyne cycloaddition with phenylacetylene, alkynyl-3β-cholesterol and cobalt/iron bis(dicarbollide) terminal alkynes to form the target 1,2,3-triazoles. The -carborane-cholesterol conjugate 9-3β-Chol-O(CH)C-CH-N(CH)MeN--7,8-CBH with charge-compensated group in a linker can be used as a precursor for preparation of liposomes for Boron Neutron Capture Therapy (BNCT). A series of novel zwitter-ionic boron-enriched cluster compounds bearing a 1,2,3-triazol-metallacarborane-carborane conjugated system was synthesized. Prepared conjugates contain a large amount of boron atom in the biomolecule and potentially can be used for BNCT.