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

Alexander Aleksandrovich Alexeev 1
Alexander Aleksandrovich Alexeev
, 
Evgeniya Vladimirovna Nurieva 1
Evgeniya Vladimirovna Nurieva
, 
Tatiana Petrovna Trofimova 1, 2
Tatiana Petrovna Trofimova
, 
Ekaterina Aleksandrovna Chesnakova 3
Ekaterina Aleksandrovna Chesnakova
,  , 
Konstantin Alexandrovich Lyssenko 1, 4
Konstantin Alexandrovich Lyssenko
, 
Marina Vladimirovna Filimonova 3
Marina Vladimirovna Filimonova
, 
Ol'ga Nikolaevna Zefirova 1, 2
Ol'ga Nikolaevna Zefirova
10.1016/j.mencom.2019.01.003
Published 2018-12-28
Communication , Volume 29, Issue 1, 14-16
12
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Alexeev A. A. et al. Bicyclic bridged isothioureas: synthesis and evaluation of activity in a model of lipopolysaccharide-induced septic shock // Mendeleev Communications. 2018. Vol. 29. No. 1. pp. 14-16.
GOST all authors (up to 50) Copy
Alexeev A. A., Nurieva E. V., Trofimova T. P., Chesnakova E. A., Grishin Y. K., Lyssenko K. A., Filimonova M. V., Zefirova O. N. Bicyclic bridged isothioureas: synthesis and evaluation of activity in a model of lipopolysaccharide-induced septic shock // Mendeleev Communications. 2018. Vol. 29. No. 1. pp. 14-16.
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TY - JOUR
DO - 10.1016/j.mencom.2019.01.003
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.01.003
TI - Bicyclic bridged isothioureas: synthesis and evaluation of activity in a model of lipopolysaccharide-induced septic shock
T2 - Mendeleev Communications
AU - Alexeev, Alexander Aleksandrovich
AU - Nurieva, Evgeniya Vladimirovna
AU - Trofimova, Tatiana Petrovna
AU - Chesnakova, Ekaterina Aleksandrovna
AU - Grishin, Yuri Konstantinovich
AU - Lyssenko, Konstantin Alexandrovich
AU - Filimonova, Marina Vladimirovna
AU - Zefirova, Ol'ga Nikolaevna
PY - 2018
DA - 2018/12/28
PB - Mendeleev Communications
SP - 14-16
IS - 1
VL - 29
ER -
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@article{2018_Alexeev,
author = {Alexander Aleksandrovich Alexeev and Evgeniya Vladimirovna Nurieva and Tatiana Petrovna Trofimova and Ekaterina Aleksandrovna Chesnakova and Yuri Konstantinovich Grishin and Konstantin Alexandrovich Lyssenko and Marina Vladimirovna Filimonova and Ol'ga Nikolaevna Zefirova},
title = {Bicyclic bridged isothioureas: synthesis and evaluation of activity in a model of lipopolysaccharide-induced septic shock},
journal = {Mendeleev Communications},
year = {2018},
volume = {29},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.01.003},
number = {1},
pages = {14--16},
doi = {10.1016/j.mencom.2019.01.003}
}
MLA
Cite this
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Alexeev, Alexander Aleksandrovich, et al. “Bicyclic bridged isothioureas: synthesis and evaluation of activity in a model of lipopolysaccharide-induced septic shock.” Mendeleev Communications, vol. 29, no. 1, Dec. 2018, pp. 14-16. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.01.003.

Abstract

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-aza-bicyclo[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.

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