A. A. Alexeev, E. V. Nurieva, T. P. Trofimova, E. A. Chesnakova, Yu. K. Grishin, K. A. Lyssenko, M. V. Filimonova, O. N. Zefirova, “Bicyclic bridged isothioureas: synthesis and evaluation of activity in a model of lipopolysaccharide-induced septic shock”, Mendeleev Commun., 2019, том 29, выпуск 1,страницы 14

Эта публикация цитируется в 9 статьях

Bicyclic bridged isothioureas: synthesis and evaluation of activity in a model of lipopolysaccharide-induced septic shock

A. A. Alexeev^a, E. V. Nurieva^a, T. P. Trofimova^ab, E. A. Chesnakova^c, Yu. K. Grishin^a, K. A. Lyssenko^ad, M. V. Filimonova^c, O. N. Zefirova^ab

^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 Medical Radiology Research Center, Russian Academy of Medical Sciences, Obninsk, Kaluga Region, Russian Federation
^d A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Moscow, Russian Federation

Аннотация: A convenient synthetic pathway to bridged isothioureas via cyclization of tert-butyl-substituted cyclohex-3-en-1-ylthiourea by the action of bromine has been developed. The effective use of tert-butyl protective group was demonstrated, and the crystal structure of synthesized (3aRS,7SR,7aRS)-7-bromo-3a,4,5,6,7,7a-hexahydro-1,3-benzothiazol-2-amine hydrobromide was determined by X-ray analysis. (1RS,5SR)-2-Thia-4-azabicyclo[3.3.1]non-3-en-3-amine as a strong inducible nitric oxide synthase inhibitor in vitro surprisingly caused additional hypotension in LPS-induced acute endotoxic shock model while its C8-hydroxy-derivative displayed prominent and durable vasoconstrictive effect.

Язык публикации: английский

DOI: 10.1016/j.mencom.2019.01.003