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JOURNALS // Mendeleev Communications // Archive

Mendeleev Commun., 2013 Volume 23, Issue 2, Pages 76–77 (Mi mendc2618)

This article is cited in 11 papers

Synthesis of 2-thia-4-azabicyclo[3.3.1]non-3-en-3-amine – bridged nitric oxide synthase inhibitor with enhanced lipophilicity

O. N. Zefirovaab, E. D. Plotnikovaa, E. V. Nurievaa, D. I. Peregudc, M. V. Onufrievd, N. V. Gulyaevad

a Department of Chemistry, M.V. Lomonosov Moscow State University, Moscow, Russian Federation
b Institute of Physiologically Active Compounds, Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry, Russian Academy of Sciences, Chernogolovka, Moscow Region, Russian Federation
c National Research Center on Addictions, Ministry of Health and Social Development of the Russian Federation, Moscow, Russian Federation
d Institute for Higher Nervous Activity and Neurophysiology, Russian Academy of Sciences, Moscow, Russian Federation

Abstract: 2-Thia-4-azabicyclo[3.3.1]non-3-en-3-amine was synthesized as a lipophilic analogue of NO-synthase inhibitor 2-amino-5,6-dihydro- 4H-1,3-thiazine and found to be a potent inhibitor of inducible NO-synthase in vitro. The crystal structure of the key intermediate 2-thia-4-azabicyclo[3.3.1]nonane-3-thione (obtained by cyclization of trans-3-bromocyclohexylamine with carbon disulfide) was determined by X-ray analysis.

Language: English

DOI: 10.1016/j.mencom.2013.03.006



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