Synthesis and Structure of Nido-Carboranyl Azide and Its “Click” Reactions

Druzina, Anna A.; Zhidkova, Olga B.; Dudarova, Nadezhda V.; Kosenko, Irina D.; Ananyev, Ivan V.; Timofeev, Sergey V.; Bregadze, Vladimir I.

doi:10.3390/molecules26030530

Open AccessArticle

Synthesis and Structure of Nido-Carboranyl Azide and Its “Click” Reactions

by

Anna A. Druzina

^*

,

Olga B. Zhidkova

,

Nadezhda V. Dudarova

,

Irina D. Kosenko

,

Ivan V. Ananyev

,

Sergey V. Timofeev

and

Vladimir I. Bregadze

A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119991 Moscow, Russia

^*

Author to whom correspondence should be addressed.

Molecules 2021, 26(3), 530; https://doi.org/10.3390/molecules26030530

Submission received: 30 December 2020 / Revised: 15 January 2021 / Accepted: 15 January 2021 / Published: 20 January 2021

(This article belongs to the Special Issue Frontiers of Boron Chemistry in 21th Century: From Fundamental Science to Applications - In Memory of Professor M. Frederick Hawthorne)

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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.

Keywords: nido-carborane; boronated azide; cobalt bis(dicarbollide); “click” reaction; cholesterol; X-ray diffraction

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MDPI and ACS Style

Druzina, A.A.; Zhidkova, O.B.; Dudarova, N.V.; Kosenko, I.D.; Ananyev, I.V.; Timofeev, S.V.; Bregadze, V.I. Synthesis and Structure of Nido-Carboranyl Azide and Its “Click” Reactions. Molecules 2021, 26, 530. https://doi.org/10.3390/molecules26030530

AMA Style

Druzina AA, Zhidkova OB, Dudarova NV, Kosenko ID, Ananyev IV, Timofeev SV, Bregadze VI. Synthesis and Structure of Nido-Carboranyl Azide and Its “Click” Reactions. Molecules. 2021; 26(3):530. https://doi.org/10.3390/molecules26030530

Chicago/Turabian Style

Druzina, Anna A., Olga B. Zhidkova, Nadezhda V. Dudarova, Irina D. Kosenko, Ivan V. Ananyev, Sergey V. Timofeev, and Vladimir I. Bregadze. 2021. "Synthesis and Structure of Nido-Carboranyl Azide and Its “Click” Reactions" Molecules 26, no. 3: 530. https://doi.org/10.3390/molecules26030530

APA Style

Druzina, A. A., Zhidkova, O. B., Dudarova, N. V., Kosenko, I. D., Ananyev, I. V., Timofeev, S. V., & Bregadze, V. I. (2021). Synthesis and Structure of Nido-Carboranyl Azide and Its “Click” Reactions. Molecules, 26(3), 530. https://doi.org/10.3390/molecules26030530

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Synthesis and Structure of Nido-Carboranyl Azide and Its “Click” Reactions

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