Methyltrioxorhenium catalysed synthesis of highly oxidised aryltetralin lignans with anti-topoisomerase II and apoptogenic activities
Author(s)
Date Issued
2005
Type
Article
Abstract
A novel and efficient procedure to prepare highly oxidised aryltetralin lignans, such as isopodophyllotoxone and (-)-aristologone
derivatives, by oxidation of podophyllotoxin and galbulin with methylrhenium trioxide (MTO) and novel MTO heterogeneous
catalysts is reported. It is noteworthy that in the case of isopodophyllotoxone derivatives the functionalisation of the
C-4 position of the C-ring and the ring-opening of the D-lactone moiety increased the activity against topoisomerase II while causing
the undesired inhibition of tubulin polymerisation to disappear. The novel (-)-aristologone derivatives showed apoptogenic
activity against resistant human lymphoma cell lines.
Additional information
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Citation
Saladino, R. et al. 2005. Methyltrioxorhenium catalysed synthesis of highly oxidised aryltetralin lignans with anti-topoisomerase II and apoptogenic activities. "Bioorganic & Medicinal Chemistry" 13: 5949–5960
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