Synthesis of novel non-natural spiro[2.3]hexane amino acids, the conformationally restricted analogs of γ-aminobutyric acid
- Authors: Yashin N.V.1,2, Averina E.B.1,2, Vasilenko D.A.1, Grishin Y.K.1, Osolodkin D.I.1,3, Palyulin V.A.1,2, Kuznetsova T.S.1, Zefirov N.S.1,2
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Affiliations:
- M. V. Lomonosov Moscow State University, Department of Chemistry
- Institute of Physiologically Active Compounds, Russian Academy of Sciences
- Institute of Poliomyelitis and Viral Encephalitis, M. P. Chumakov Federal Scientific Center for Research and Development of Immune-and-Biological Products, Russian Academy of Sciences
- Issue: Vol 66, No 8 (2017)
- Pages: 1483-1490
- Section: Full Articles
- URL: https://journals.rcsi.science/1066-5285/article/view/241123
- DOI: https://doi.org/10.1007/s11172-017-1912-7
- ID: 241123
Cite item
Abstract
3-Methylenecyclobutanecarboxylic acid and its methyl ester were used as the starting compounds for the synthesis of new spiro[2.3]hexane amino acids, the conformationally rigid analogs of γ-aminobutyric acid, namely, 5-aminospiro[2.3]hexanecarboxylic and 5-amino-spiro[2.3]hexanephosphonic acids, promising modulators of GABAergic cascades in the human central nervous system. The methods developed for the synthesis of the target amino acids are based on the reactions of catalytic [1+2] cycloaddition of diazoacetic and diazophosphonic esters to 3-substituted methylenecyclobutanes, as well as on a modified Curtius reaction for the transformation of a carboxy group to the amine one.
About the authors
N. V. Yashin
M. V. Lomonosov Moscow State University, Department of Chemistry; Institute of Physiologically Active Compounds, Russian Academy of Sciences
Email: elaver@med.chem.msu.ru
Russian Federation, Build. 3, 1 Leninskie Gory, Moscow, 119991; 1 Severnyi proezd, Chernogolovka, Moscow Region, 142432
E. B. Averina
M. V. Lomonosov Moscow State University, Department of Chemistry; Institute of Physiologically Active Compounds, Russian Academy of Sciences
Author for correspondence.
Email: elaver@med.chem.msu.ru
Russian Federation, Build. 3, 1 Leninskie Gory, Moscow, 119991; 1 Severnyi proezd, Chernogolovka, Moscow Region, 142432
D. A. Vasilenko
M. V. Lomonosov Moscow State University, Department of Chemistry
Email: elaver@med.chem.msu.ru
Russian Federation, Build. 3, 1 Leninskie Gory, Moscow, 119991
Yu. K. Grishin
M. V. Lomonosov Moscow State University, Department of Chemistry
Email: elaver@med.chem.msu.ru
Russian Federation, Build. 3, 1 Leninskie Gory, Moscow, 119991
D. I. Osolodkin
M. V. Lomonosov Moscow State University, Department of Chemistry; Institute of Poliomyelitis and Viral Encephalitis, M. P. Chumakov Federal Scientific Center for Research and Development of Immune-and-Biological Products, Russian Academy of Sciences
Email: elaver@med.chem.msu.ru
Russian Federation, Build. 3, 1 Leninskie Gory, Moscow, 119991; Domovladeniye 8, Str. 1, poselok Instituta Poliomielita, Poseleniye Moskovsky, Moscow, 108819
V. A. Palyulin
M. V. Lomonosov Moscow State University, Department of Chemistry; Institute of Physiologically Active Compounds, Russian Academy of Sciences
Email: elaver@med.chem.msu.ru
Russian Federation, Build. 3, 1 Leninskie Gory, Moscow, 119991; 1 Severnyi proezd, Chernogolovka, Moscow Region, 142432
T. S. Kuznetsova
M. V. Lomonosov Moscow State University, Department of Chemistry
Email: elaver@med.chem.msu.ru
Russian Federation, Build. 3, 1 Leninskie Gory, Moscow, 119991
N. S. Zefirov
M. V. Lomonosov Moscow State University, Department of Chemistry; Institute of Physiologically Active Compounds, Russian Academy of Sciences
Email: elaver@med.chem.msu.ru
Russian Federation, Build. 3, 1 Leninskie Gory, Moscow, 119991; 1 Severnyi proezd, Chernogolovka, Moscow Region, 142432