Journal
ORGANIC LETTERS
Volume 17, Issue 12, Pages 3118-3121Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b01419
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Funding
- Natural Science Foundation of China [21132009]
- National Science and Technology Project of China [2012ZX09301-002]
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To investigate the effects of configuration on bioactivity, spirooliganones A and B and their six diastereoisomers (1-8) were synthesized in 11 steps. The key benzopyran core was assembled by intermolecular [4 + 2] hetero-Diels-Alder cycloaddition between (-)-sabinene and o-quinone methide, which was generated from the corresponding o-hydroxybenzyl alcohol. After establishing the absolute configuration, the inhibitory activities of spirooliganones 1-8 against Coxsackie virus B3 were evaluated, and the primary structure-activity relationships were analyzed. Compound 3 was the most potent compound, with an IC50 of 0.41 mu M.
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