Novel Cobalt Bis(dicarbollide) Based on Terminal Alkynes and Their Click-Reactions

被引:11
作者
Druzina, Anna A. [1 ]
Kosenko, Irina D. [1 ]
Zhidkova, Olga B. [1 ]
Ananyev, Ivan V. [1 ,2 ]
Timofeev, Sergey V. [1 ]
Bregadze, Vladimir I. [1 ]
机构
[1] Russian Acad Sci, AN Nesmeyanov Inst Organoelement Cpds, Vavilov Str 28, Moscow 119991, Russia
[2] Natl Res Univ Higher Sch Econ, Myasnitskaya Str 20, Moscow 101000, Russia
基金
俄罗斯基础研究基金会;
关键词
Alkynes; Cholesterol; Click" reaction; Cobalt and iron bis(dicarbollide); Lipids; Metallacarboranes; Polyhedral boron hydrides; X-ray diffraction studies; NEUTRON-CAPTURE THERAPY; MEDICINAL CHEMISTRY; BORON; DERIVATIVES; CYCLOADDITION; ANION; METALLACARBORANES; PHARMACOPHORES; LIGATION; DELIVERY;
D O I
10.1002/ejic.202000388
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Novel cobalt bis(dicarbollide) terminal alkynes with charge-compensated group were synthesized by the cleavage reactions of oxonium derivatives of cobalt bis(dicarbollide) with N,N-dimethylprop-2-yn-1-amine. The solid-state molecular structures of alkynes prepared from 1,4-dioxane and tetrahydropyran derivatives of cobalt and iron bis(dicarbollide) were determined by single-crystal X-ray diffraction. A series of zwitterionic conjugates of cobalt/iron bis(dicarbollide) with cholesterol were prepared using the copper(I)-catalyzed azide-alkyne cycloaddition reaction.
引用
收藏
页码:2658 / 2665
页数:8
相关论文
共 76 条
[1]   Toward reliable density functional methods without adjustable parameters: The PBE0 model [J].
Adamo, C ;
Barone, V .
JOURNAL OF CHEMICAL PHYSICS, 1999, 110 (13) :6158-6170
[2]   Gabedit-A Graphical User Interface for Computational Chemistry Softwares [J].
Allouche, Abdul-Rahman .
JOURNAL OF COMPUTATIONAL CHEMISTRY, 2011, 32 (01) :174-182
[3]   Toward a Rigorous Definition of a Strength of Any Interaction Between Bader's Atomic Basins [J].
Ananyev, Ivan V. ;
Karnoukhova, Valentina A. ;
Dmitrienko, Artem O. ;
Lyssenko, Konstantin A. .
JOURNAL OF PHYSICAL CHEMISTRY A, 2017, 121 (23) :4517-4522
[4]  
[Anonymous], 2020, ANGEW CHEM
[5]  
[Anonymous], 1993, ANGEW CHEM, DOI DOI 10.1002/ANGE.19931050705
[6]  
Avdeef Alex, 2001, Current Topics in Medicinal Chemistry, V1, P277, DOI 10.2174/1568026013395100
[7]   A Theta-Shaped Amphiphilic Cobaltabisdicarbollide Anion: Transition From Monolayer Vesicles to Micelles [J].
Bauduin, Pierre ;
Prevost, Sylvain ;
Farras, Pau ;
Teixidor, Francesc ;
Diat, Olivier ;
Zemb, Thomas .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (23) :5298-5300
[8]   Towards new boron carriers for boron neutron capture therapy: Metallacarboranes bearing cobalt, iron and chromium and their cholesterol conjugates [J].
Bialek-Pietras, Magdalena ;
Olejniczak, Agnieszka B. ;
Tachikawa, Shoji ;
Nakamura, Hiroyuki ;
Lesnikowski, Zbigniew J. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2013, 21 (05) :1136-1142
[9]  
Bregadze VI, 2012, BORON SCIENCE: NEW TECHNOLOGIES AND APPLICATIONS, P181
[10]   Novel types of boronated chlorin e6 conjugates via 'click chemistry' [J].
Bregadze, Vladimir I. ;
Semioshkin, Andrey A. ;
Las'kova, Julia N. ;
Berzina, Maria Ya. ;
Lobanova, Irina A. ;
Sivaev, Igor B. ;
Grin, Mikhail A. ;
Titeev, Rustam A. ;
Brittal, Dmitry I. ;
Ulybina, Olga V. ;
Chestnova, Anastasija V. ;
Ignatova, Anastasija A. ;
Feofanov, Alexey V. ;
Mironov, Andrey F. .
APPLIED ORGANOMETALLIC CHEMISTRY, 2009, 23 (09) :370-374