title: Stereoselective Construction of 2,7-Disubstituted fused-Bis Tetrahydrofuran Skeletons: Biomimetic-Type Synthesis and Biological Evaluation of (±)- and (-)-Aplysiallene and Their Derivatives.
abstract: A series of trans/trans and cis/cis fused-bis tetrahydrofuran compounds have been obtained stereoselectively in high yields via a one-pot operation involving the intramolecular haloetherification of (Z,Z)-diene diol 19a and (E,E)-diene disilylether 19d, respectively. This method was subsequently applied to the biomimetic-type synthesis of (±)- and (-)-aplysiallene. The inhibitory activities of these compounds and their bromodiene isomers toward Na(+)/K(+) ATPase were determined in vitro, and gave IC50 values of approximately 15 μM in all cases.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Osaka University , 1-6, Yamada-oka, Suita, Osaka 565-0871, Japan.
authors.forename: Maki
authors.initials: M
authors.lastname: Yamakawa
authors.affiliation: Graduate School of Pharmaceutical Sciences, Osaka University , 1-6, Yamada-oka, Suita, Osaka 565-0871, Japan.
authors.forename: Takeshi
authors.initials: T
authors.lastname: Kurachi
authors.affiliation: Graduate School of Pharmaceutical Sciences, Osaka University , 1-6, Yamada-oka, Suita, Osaka 565-0871, Japan.
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Yoshikawa
authors.affiliation: Graduate School of Pharmaceutical Sciences, Osaka University , 1-6, Yamada-oka, Suita, Osaka 565-0871, Japan.
authors.forename: Mitsuhiro
authors.initials: M
authors.lastname: Arisawa
authors.affiliation: Graduate School of Dental Medicine, Hokkaido University , Kita-13 Nishi-7, Kitaku, Sapporo, Hokkaido 060-8586, Japan.
authors.forename: Yuichiro
authors.initials: Y
authors.lastname: Okino
authors.affiliation: Graduate School of Dental Medicine, Hokkaido University , Kita-13 Nishi-7, Kitaku, Sapporo, Hokkaido 060-8586, Japan.
authors.forename: Kuniaki
authors.initials: K
authors.lastname: Suzuki
authors.affiliation: Graduate School of Pharmaceutical Sciences, Osaka University , 1-6, Yamada-oka, Suita, Osaka 565-0871, Japan.
authors.forename: Hiromichi
authors.initials: H
authors.lastname: Fujioka
mesh_terms: D032701:Biomimetics; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry* / Q000494:pharmacology*; D004791:Enzyme Inhibitors / Q000737:chemistry* / Q000494:pharmacology*; D005663:Furans / Q000737:chemistry* / Q000494:pharmacology*; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D000254:Sodium-Potassium-Exchanging ATPase / Q000037:antagonists & inhibitors* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D019086:Bridged Bicyclo Compounds, Heterocyclic; D004791:Enzyme Inhibitors; D005663:Furans; C432927:aplysiallene; C018674:tetrahydrofuran; D000254:Sodium-Potassium-Exchanging ATPase