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Synthesis and Biological Evaluation of 7‐Deoxy Analogues of the Human Rhinovirus 3C Protease Inhibitor Thysanone
Author(s) -
Schünemann Katrin,
Furkert Daniel P.,
Connelly Stephen,
Fraser John D.,
Sperry Jonathan,
Brimble Margaret A.
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301515
Subject(s) - chemistry , rhinovirus , protease , enzyme , biological activity , chemical synthesis , stereochemistry , enzyme inhibitor , protease inhibitor (pharmacology) , combinatorial chemistry , biochemistry , virus , in vitro , virology , antiretroviral therapy , viral load , biology
The synthesis of (±)‐7‐deoxythysanone and three analogues has been developed. The key oxa‐Pictet–Spengler reaction enabled the synthesis of the naphthopyran precursor, which could be readily converted to 7‐deoxythysanone and three related analogues. The biological activity of these compounds was also evaluated against HRV 3C protease, the results of which suggest that inhibition of the enzyme requires the presence of the 7‐oxa functionality.