Synthesis of isosteric analogues of rooperol
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Hypoxoside is a norlignan bisglycoside derived from Hypoxis hemerocallidae (African potato), a medicinal plant used in Africa to treat a variety of disorders, including cancer, cardiac diseases, immune disfunction, inflammation, and prostate hyperplasia. Its aglycone form, (1,5-bis(3’,4’-dihydroxyphenyl)pent-1-en-4-yne (rooperol) is produced in the presence of β-glucosidase which is present in the GI lumen, leading investigators to evaluate hypososide as a potential oral prodrug. Unfortunately, the presence of catechol moieties results in extensive phase II metabolism before therapeutic blood concentrations are achieved. One approach to address this obstacle is to replace the catechols with isosteres which may be more metabolically stable and possess the same bioactivity. This body of work is focused on the synthesis of rooperol and three analogues of rooperol of which the catechol moieties are replaced with a small set of isosteres.