| Literature DB >> 29098212 |
D R Hirsch1, D V Schiavone, A J Berkowitz, L A Morrison, T Masaoka, J A Wilson, E Lomonosova, H Zhao, B S Patel, S H Datla, S G Hoft, S J Majidi, R K Pal, E Gallicchio, L Tang, J E Tavis, S F J Le Grice, J A Beutler, R P Murelli.
Abstract
3,7-Dihydroxytropolones (3,7-dHTs) are highly oxygenated troponoids that have been identified as lead compounds for several human diseases. To date, structure-function studies on these molecules have been limited due to a scarcity of synthetic methods for their preparation. New synthetic strategies towards structurally novel 3,7-dHTs would be valuable in further studying their therapeutic potential. Here we describe the successful adaptation of a [5 + 2] oxidopyrilium cycloaddition/ring-opening for 3,7-dHT synthesis, which we apply in the synthesis of a plausible biosynthetic intermediate to the natural products puberulic and puberulonic acid. We have also tested these new compounds in several biological assays related to human immunodeficiency virus (HIV), hepatitis B virus (HBV) and herpes simplex virus (HSV) in order to gain insight into structure-functional analysis related to antiviral troponoid development.Entities:
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Year: 2017 PMID： 29098212 PMCID： PMC5748270 DOI： 10.1039/c7ob02453c
Source DB: PubMed Journal: Org Biomol Chem ISSN： 1477-0520 Impact factor: 3.876