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Discovery of a New Class of Inhibitors of Vaccinia Virus Based on (−)‐Borneol from Abies sibirica and (+)‐Camphor
Author(s) -
Sokolova Anastasiya S.,
Yarovaya Olga I.,
Bormotov Nikolay I.,
Shishkina Larisa N.,
Salakhutdinov Nariman F.
Publication year - 2018
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201800153
Subject(s) - chemistry , morpholine , camphor , heptane , vaccinia , cytotoxicity , bioassay , amide , stereochemistry , alkyne , virus , inhibitory postsynaptic potential , in vitro , combinatorial chemistry , organic chemistry , biochemistry , virology , catalysis , genetics , biology , gene , recombinant dna , neuroscience
A series of the bornyl ester/amide derivatives with N‐containing heterocycles were designed and synthesized as vaccinia virus ( VV ) inhibitors. Bioassay results showed that among the designed compounds, derivatives 6 , 13 , 14 , 34 , 36 and 37 showed the best inhibitory activity against VV with the IC 50 values of 12.9, 17.9, 3.4, 2.5, 12.5 and 7.5 μ m , respectively, and good cytotoxicity. The primary structure–activity relationship ( SAR ) study suggested that the combination of a saturated N‐heterocycle, such as morpholine or 4‐methylpiperidine, and a 1,7,7‐trimethylbicyclo[2.2.1]heptane scaffold was favorable for antiviral activity.