Regioselective oxidative fragmentation of drimanic terpene alcohols: a short, easy and efficient access to natural and synthetic 11-nordrimane terpene derivatives

Cuéllar, Mauricio; Moreno, Luis; Preite, Marcelo D.

doi:10.3998/ark.5550190.0004.a17

Cited by 10 publications

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Synthetic and Biological Studies of Sesquiterpene Polygodial: Activity of 9‐Epipolygodial against Drug‐Resistant Cancer Cells

et al. 2015

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Polygodial, a terpenenoid dialdehyde isolated from Polygonum hydropiper L., is a known TRPV1 agonist. In this investigation a series of polygodial analogues were prepared and investigated for TRPV1 agonistic and anticancer activities. These experiments led to the identification of 9-epipolygodial, possessing antiproliferative potency significantly exceeding that of polygodial. Epipolygodial maintained potency against apoptosis-resistant cancer cells as well as those displaying the MDR phenotype. In addition, a chemical feasibility for the previously proposed mechanism of action of polygodial, involving the Paal-Knorr pyrrole formation with a lysine residue on the target protein, was demonstrated through the synthesis of a stable polygodial pyrrole derivative. These studies reveal rich chemical and biological properties associated with polygodial and its direct derivatives. They should inspire further work in this area aimed at the development of new pharmacological agents or exploration of novel mechanisms of covalent modification of biological molecules with natural products.

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Synthetic and Biological Studies of Sesquiterpene Polygodial: Activity of 9‐Epipolygodial against Drug‐Resistant Cancer Cells

et al. 2015

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LTA‐mediated synthesis and complete assignment of ¹H and ¹³C NMR data of two natural 11‐nordrimanes: isonordrimenone and polygonone

Moreno‐Osorio

Espinoza

Cuéllar

et al. 2007

Magnetic Reson in Chemistry

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Isolation and characterization of two new drimanes from Zygogynum baillonii and synthesis of analogues

et al. 2008

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Regioselective oxidative fragmentation of drimanic terpene alcohols: a short, easy and efficient access to natural and synthetic 11-nordrimane terpene derivatives

Abstract: Using selective Cr(VI) oxidations with Jones reagent and PCC, a regioselective and direct access to different oxygenated 11-nordrimane skeletons was achieved, in good overall yield, starting from naturally occurring drimane terpenes.

Cited by 10 publications

References 22 publications

Synthetic and Biological Studies of Sesquiterpene Polygodial: Activity of 9‐Epipolygodial against Drug‐Resistant Cancer Cells

Synthetic and Biological Studies of Sesquiterpene Polygodial: Activity of 9‐Epipolygodial against Drug‐Resistant Cancer Cells

LTA‐mediated synthesis and complete assignment of ¹H and ¹³C NMR data of two natural 11‐nordrimanes: isonordrimenone and polygonone

Isolation and characterization of two new drimanes from Zygogynum baillonii and synthesis of analogues

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Regioselective oxidative fragmentation of drimanic terpene alcohols: a short, easy and efficient access to natural and synthetic 11-nordrimane terpene derivatives

Abstract: Using selective Cr(VI) oxidations with Jones reagent and PCC, a regioselective and direct access to different oxygenated 11-nordrimane skeletons was achieved, in good overall yield, starting from naturally occurring drimane terpenes.

Cited by 10 publications

References 22 publications

Synthetic and Biological Studies of Sesquiterpene Polygodial: Activity of 9‐Epipolygodial against Drug‐Resistant Cancer Cells

Synthetic and Biological Studies of Sesquiterpene Polygodial: Activity of 9‐Epipolygodial against Drug‐Resistant Cancer Cells

LTA‐mediated synthesis and complete assignment of 1H and 13C NMR data of two natural 11‐nordrimanes: isonordrimenone and polygonone

Isolation and characterization of two new drimanes from Zygogynum baillonii and synthesis of analogues

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LTA‐mediated synthesis and complete assignment of ¹H and ¹³C NMR data of two natural 11‐nordrimanes: isonordrimenone and polygonone