Synthesis and Structure of <i>Nido</i>-Carboranyl Azide and Its “Click” Reactions

Synthesis and Structure of <i>Nido</i>-Carboranyl Azide and Its “Click” Reactions

Novel<b> </b>zwitter-ionic<b> </b><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&l...

Full description

Bibliographic Details
Main Authors: Anna А. Druzina, Olga B. Zhidkova, Nadezhda V. Dudarova, Irina D. Kosenko, Ivan V. Ananyev, Sergey V. Timofeev, Vladimir I. Bregadze
Format: Article
Language:English
Published: MDPI AG 2021-01-01
Series:Molecules
Subjects:
<i>nido</i>-carborane
boronated azide
cobalt bis(dicarbollide)
“click” reaction
cholesterol
X-ray diffraction
Online Access:https://www.mdpi.com/1420-3049/26/3/530
id doaj-5572c81062b84322a54c018d34883ea2
record_format Article
spelling doaj-5572c81062b84322a54c018d34883ea22021-01-21T00:05:24ZengMDPI AGMolecules1420-30492021-01-012653053010.3390/molecules26030530Synthesis and Structure of <i>Nido</i>-Carboranyl Azide and Its “Click” ReactionsAnna А. Druzina0Olga B. Zhidkova1Nadezhda V. Dudarova2Irina D. Kosenko3Ivan V. Ananyev4Sergey V. Timofeev5Vladimir I. Bregadze6A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119991 Moscow, RussiaA.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119991 Moscow, RussiaA.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119991 Moscow, RussiaA.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119991 Moscow, RussiaA.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119991 Moscow, RussiaA.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119991 Moscow, RussiaA.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119991 Moscow, RussiaNovel<b> </b>zwitter-ionic<b> </b><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>N-<i>nido</i>-7,8-C<sub>2</sub>B<sub>9</sub>H<sub>11</sub> 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 <i>nido</i>-carborane-cholesterol conjugate 9-3β-Chol-O(CH<sub>2</sub>)С-CH-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>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.https://www.mdpi.com/1420-3049/26/3/530<i>nido</i>-carboraneboronated azidecobalt bis(dicarbollide)“click” reactioncholesterolX-ray diffraction
collection DOAJ
language English
format Article
sources DOAJ
author Anna А. Druzina
Olga B. Zhidkova
Nadezhda V. Dudarova
Irina D. Kosenko
Ivan V. Ananyev
Sergey V. Timofeev
Vladimir I. Bregadze
spellingShingle Anna А. Druzina
Olga B. Zhidkova
Nadezhda V. Dudarova
Irina D. Kosenko
Ivan V. Ananyev
Sergey V. Timofeev
Vladimir I. Bregadze
Synthesis and Structure of <i>Nido</i>-Carboranyl Azide and Its “Click” Reactions
Molecules
<i>nido</i>-carborane
boronated azide
cobalt bis(dicarbollide)
“click” reaction
cholesterol
X-ray diffraction
author_facet Anna А. Druzina
Olga B. Zhidkova
Nadezhda V. Dudarova
Irina D. Kosenko
Ivan V. Ananyev
Sergey V. Timofeev
Vladimir I. Bregadze
author_sort Anna А. Druzina
title Synthesis and Structure of <i>Nido</i>-Carboranyl Azide and Its “Click” Reactions
title_short Synthesis and Structure of <i>Nido</i>-Carboranyl Azide and Its “Click” Reactions
title_full Synthesis and Structure of <i>Nido</i>-Carboranyl Azide and Its “Click” Reactions
title_fullStr Synthesis and Structure of <i>Nido</i>-Carboranyl Azide and Its “Click” Reactions
title_full_unstemmed Synthesis and Structure of <i>Nido</i>-Carboranyl Azide and Its “Click” Reactions
title_sort synthesis and structure of <i>nido</i>-carboranyl azide and its “click” reactions
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2021-01-01
description Novel<b> </b>zwitter-ionic<b> </b><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>N-<i>nido</i>-7,8-C<sub>2</sub>B<sub>9</sub>H<sub>11</sub> 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 <i>nido</i>-carborane-cholesterol conjugate 9-3β-Chol-O(CH<sub>2</sub>)С-CH-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>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.
topic <i>nido</i>-carborane
boronated azide
cobalt bis(dicarbollide)
“click” reaction
cholesterol
X-ray diffraction
url https://www.mdpi.com/1420-3049/26/3/530
work_keys_str_mv AT annaadruzina synthesisandstructureofinidoicarboranylazideanditsclickreactions
AT olgabzhidkova synthesisandstructureofinidoicarboranylazideanditsclickreactions
AT nadezhdavdudarova synthesisandstructureofinidoicarboranylazideanditsclickreactions
AT irinadkosenko synthesisandstructureofinidoicarboranylazideanditsclickreactions
AT ivanvananyev synthesisandstructureofinidoicarboranylazideanditsclickreactions
AT sergeyvtimofeev synthesisandstructureofinidoicarboranylazideanditsclickreactions
AT vladimiribregadze synthesisandstructureofinidoicarboranylazideanditsclickreactions
_version_ 1724330384905207808

Similar Items