Synthesis of novel carboranyl azides and "click" reactions thereof.

Novel nido -carboranyl azide [7-N 3 CH 2 CH 2 OCH 2 CH 2 O-7,8-C 2 B 9 H 11 - was prepared by the reaction of 1-hydroxy- ortho -carborane with bis(2-chloroethyl) ether followed by the conversion to its nido -form and reactions with sodium iodide and sodium azide. Previously undescribed carboranyl azides 1-N 3 CH 2 CH 2 OCH 2 CH 2 S-1,2-C 2 B 10 H 11 and [7-N 3 CH 2 CH 2 OCH 2 CH 2 S-7,8-C 2 B 9 H 11 - were synthesized by alkylation of trimethylammonium salt of 1-mercapto- ortho -carborane with bis(2-chloroethyl) ether followed by reactions with sodium iodide and with sodium azide and by the conversion of closo -derivative to water soluble nido -form. closo - and nido -Carboranyl azides 1-N 3 CH 2 CH 2 OCH 2 CH 2 S-1,2-C 2 B 10 H 11 and [7-N 3 CH 2 CH 2 OCH 2 CH 2 S-7,8-C 2 B 9 H 11 - were used for the copper(I)-catalyzed azide-alkyne cycloaddition with phenyacetylene. The compounds prepared can be used for the copper(I)-catalyzed сonjugation with biomolecules that act as tumor-targeting vectors for radionuclide diagnostics and boron neutron capture therapy of cancer. Image 1 • Novel carboranyl azides with diethylene glycol-like flexible spacer were synthesized. [ABSTRACT FROM AUTHOR]