Novel Squalene-Hopene Cyclase Inhibitors Derived from Hydroxycoumarins and Hydroxyacetophenones

Giancarlo Cravotto; Gianni Balliano; Silvia Tagliapietra; Simonetta Oliaro-Bosso; Gian Mario Nano

doi:10.1248/cpb.52.1171

Regular Articles

Novel Squalene-Hopene Cyclase Inhibitors Derived from Hydroxycoumarins and Hydroxyacetophenones

Giancarlo Cravotto, Gianni Balliano, Silvia Tagliapietra, Simonetta Oliaro-Bosso, Gian Mario Nano

著者情報

キーワード: 7-alkyloxycoumarin, 4-alkyloxyacetophenone, squalene hopene cyclase, oxidosqualene cyclase, secoammoresinol, secoferulenol

ジャーナルフリー

2004 年 52 巻 10 号 p. 1171-1174

DOI https://doi.org/10.1248/cpb.52.1171

詳細

抄録

Squalene-hopene cyclase (SHC) is a useful model enzyme for predicting molecular interactions with oxidosqualene cyclase (OSC). Structure–activity relationships were investigated for numerous coumarin-derived inhibitors of SHC, and structural simplifications are suggested. Both umbelliferone and 2,4-dihydroxyacetophenone provide convenient starting nuclei for the design of SHC inhibitors. Derivatives bearing an ω-epoxyfarnesyl moiety or just a plain alkyl chain showed an inhibitory effect on a recombinant SHC from Alicyclobacillus acidocaldarius expressed in Escherichia coli.

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