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Org Biomol Chem ; 16(1): 62-69, 2017 Dec 19.
Artículo en Inglés | MEDLINE | ID: mdl-29098212

RESUMEN

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.


Asunto(s)
Antivirales/farmacología , VIH/efectos de los fármacos , Virus de la Hepatitis B/efectos de los fármacos , Simplexvirus/efectos de los fármacos , Tropolona/análogos & derivados , Antivirales/síntesis química , Antivirales/química , Relación Dosis-Respuesta a Droga , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Relación Estructura-Actividad , Tropolona/síntesis química , Tropolona/química , Tropolona/farmacología
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