Farnesyloxycoumarins, a new class of squalene-hopene cyclase inhibitors

Giancarlo Cravotto; Gianni Balliano; Bruna Robaldo; Simonetta Oliaro-Bosso; Stefano Chimichi; Marco Boccalini

doi:10.1016/j.bmcl.2004.01.085

Farnesyloxycoumarins, a new class of squalene-hopene cyclase inhibitors

Bioorg Med Chem Lett. 2004 Apr 19;14(8):1931-4. doi: 10.1016/j.bmcl.2004.01.085.

Authors

Giancarlo Cravotto¹, Gianni Balliano, Bruna Robaldo, Simonetta Oliaro-Bosso, Stefano Chimichi, Marco Boccalini

Affiliation

¹ Dipartimento di Scienza e Tecnologia del Farmaco, Università di Torino, via Giuria 9, I-10125 Turin, Italy.

PMID: 15050630
DOI: 10.1016/j.bmcl.2004.01.085

Abstract

A few naturally occurring prenyl- and prenyloxycoumarins and several new related synthetic derivatives were evaluated as inhibitors of squalene-hopene cyclase (SHC), a useful model enzyme, to predict their interactions with oxidosqualene cyclase (OSC). Umbelliprenin-10',11'-monoepoxide (IC(50) 2.5 microM) and the corresponding 6',7'-10',11' diepoxide (IC(50) 1.5 microM) were the most active enzyme inhibitors.

MeSH terms

Bacillaceae / enzymology
Coumarins / chemical synthesis
Coumarins / classification*
Coumarins / pharmacology*
Enzyme Activation / drug effects
Enzyme Inhibitors / chemical synthesis
Enzyme Inhibitors / classification*
Enzyme Inhibitors / pharmacology*
Humans
Intramolecular Transferases / antagonists & inhibitors*
Molecular Structure
Structure-Activity Relationship

Substances

Coumarins
Enzyme Inhibitors
Intramolecular Transferases
squalene-hopene cyclase
lanosterol synthase