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

ABSTRACT: Novel zwitter-ionic nido-carboranyl azide 9-N3(CH2)3Me2N-nido-7,8-C2B9H11 was prepared by the reaction of 9-Cl(CH2)3Me2N-nido-7,8-C2B9H11 with NaN3. The solid-state molecular structure of nido-carboranyl azide was determined by single-crystal X-ray diffraction. 9-N3(CH2)3Me2N-nido-7,8-C2B9H11 was used for the copper(I)-catalyzed azide-alkyne cycloaddition with phenylacetylene, alkynyl-3?-cholesterol and cobalt/iron bis(dicarbollide) terminal alkynes to form the target 1,2,3-triazoles. The nido-carborane-cholesterol conjugate 9-3?-Chol-O(CH2)C-CH-N3(CH2)3Me2N-nido-7,8-C2B9H11 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.

SUBMITTER: Druzina AA 

PROVIDER: S-EPMC7930967 | biostudies-literature | 2021 Jan

REPOSITORIES: biostudies-literature

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Synthesis and Structure of <i>Nido</i>-Carboranyl Azide and Its "Click" Reactions.

Druzina Anna A AA   Zhidkova Olga B OB   Dudarova Nadezhda V NV   Kosenko Irina D ID   Ananyev Ivan V IV   Timofeev Sergey V SV   Bregadze Vladimir I VI  

Molecules (Basel, Switzerland) 20210120 3

Novel zwitter-ionic <i>nido</i>-carboranyl azide 9-N<sub>3</sub>(CH<sub>2</sub>)<sub>3</sub>Me<sub>2</sub>N-<i>nido</i>-7,8-C<sub>2</sub>B<sub>9</sub>H<sub>11</sub> was prepared by the reaction of 9-Cl(CH<sub>2</sub>)<sub>3</sub>Me<sub>2</sub>N-<i>nido</i>-7,8-C<sub>2</sub>B<sub>9</sub>H<sub>11</sub> with NaN<sub>3</sub>. The solid-state molecular structure of <i>nido</i>-carboranyl azide was determined by single-crystal X-ray diffraction. 9-N<sub>3</sub>(CH<sub>2</sub>)<sub>3</sub>Me<sub>2</sub  ...[more]

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