Facile Synthesis of Amino Acid Decorated Water‐Soluble Fullerene Derivatives with Anti‐influenza Activity

Author:

Bolshakova Valeriya S.12,Sinegubova Ekaterina O.3,Esaulkova Yana L.3,Peregudov Alexander S.4,Khakina Ekaterina A.45,Slesarenko Nikita A.1,Shestakov Alexander F.16,Zarubaev Vladimir V.3,Troshin Pavel A.178,Kraevaya Olga A.1

Affiliation:

1. Federal Research Center for Problems of Chemical Physics and Medicinal Chemistry of RAS Academician Semenov ave. 1 Chernogolovka 142432 Russia

2. Higher Chemical College of RAS D.I. Mendeleev University of Chemical Technology of Russia Miusskaya square 9 Moscow 125047 Russia

3. St. Petersburg Pasteur Institute Mira st. 14 St. Petersburg 197101 Russia

4. A.N. Nesmeyanov Institute of Organoelement compounds of RAS Vavylova St. 28, B‐334 Moscow 119991 Russia

5. National Research University Higher School of Economics Vavylova St. 7 Moscow 101000 Russia

6. Department of Fundamental Physics & Chemical Engineering M.V. Lomonosov Moscow State University Leninskie Gory 1/51 Moscow 119991 Russia

7. Zhengzhou Research Institute Harbin Institute of Technology Longyuan East 7th 26, Jinshui District Zhengzhou Henan 450003 China

8. Harbin Institute of Technology West Dazhi Street 92, Nan Gang District Harbin Heilongjiang 150001 China

Abstract

Comprehensive SummaryHerein, we present a facile synthesis of amide‐type water‐soluble fullerene derivatives decorated with five residues of amino acids. As compared to the previously developed approaches, the proposed method enables usage of a broad range of amino acids, including those unstable under Friedel‐Crafts reaction conditions. Furthermore, it is fully tolerant to the nature of the sixth addend X in C60R5X precursor compounds and allows one to obtain fullerene derivatives with X=Cl, H, alkyl. The synthesized amide‐type water‐soluble fullerene derivatives demonstrated promising antiviral activities against rimantadine‐resistant influenza А/Puerto Rico/8/34 (Н1N1) virus in vitro.

Funder

Russian Science Foundation

Publisher

Wiley

Subject

General Chemistry

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