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- Title
Primary Amine Nucleophilic Addition to Nitrilium Closo -Dodecaborate [B 12 H 11 NCCH 3 ] − : A Simple and Effective Route to the New BNCT Drug Design.
- Authors
Nelyubin, Alexey V.; Selivanov, Nikita A.; Bykov, Alexander Yu.; Klyukin, Ilya N.; Novikov, Alexander S.; Zhdanov, Andrey P.; Karpechenko, Natalia Yu.; Grigoriev, Mikhail S.; Zhizhin, Konstantin Yu.; Kuznetsov, Nikolay T.
- Abstract
In the present work, a convenient and straightforward approach to the preparation of borylated amidines based on the closo-dodecaborate anion [B12H11NCCH3NHR]−, R=H, Alk, Ar was developed. This method has two stages. A nitrile derivative of the general form [B12H11NCCH3]− was obtained, using a modified technique, in the first stage. On the second stage the resulting molecular system interacted with primary amines to form the target amidine products. This approach is characterised by a simple chemical apparatus, mild conditions and high yields of the final products. The mechanism of the addition of amine to the nitrile derivative of the closo-dodecaborate anion was studied, using quantum-chemical methods. The interaction between NH3 and [B12H11NCCH3]− ammonia was chosen as an example. It was found that the structure of the transition state determines the stereo-selectivity of the process. A study of the biological properties of borylated amidine sodium salts indicated that the substances had low toxicity and could accumulate in cancer cells in significant amounts.
- Subjects
DRUG design; NITRILE derivatives; AMINES; AMINE derivatives; CHEMICAL apparatus; SODIUM salts; BINOCULAR vision
- Publication
International Journal of Molecular Sciences, 2021, Vol 22, Issue 24, p13391
- ISSN
1661-6596
- Publication type
Article
- DOI
10.3390/ijms222413391