Synthesis and Structure of Nido-Carboranyl Azide and Its “Click” Reactions |
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| Authors: | Anna A. Druzina Olga B. Zhidkova Nadezhda V. Dudarova Irina D. Kosenko Ivan V. Ananyev Sergey V. Timofeev Vladimir I. Bregadze |
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| Affiliation: | A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119991 Moscow, Russia; (O.B.Z.); (N.V.D.); (I.D.K.); (I.V.A.); (S.V.T.); (V.I.B.) |
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| 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-3β-cholesterol and cobalt/iron bis(dicarbollide) terminal alkynes to form the target 1,2,3-triazoles. The nido-carborane-cholesterol conjugate 9-3β-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. |
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| Keywords: | nido-carborane, boronated azide, cobalt bis(dicarbollide), “ click” reaction, cholesterol, X-ray diffraction |
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