title: Synthesis and biological evaluation of deoxy salacinols, the role of polar substituents in the side chain on the alpha-glucosidase inhibitory activity.
abstract: Three analogs (5, 6, and 7) lacking polar substituents in the side chain of a naturally occurring alpha-glucosidase inhibitor, salacinol (1a), were synthesized by the coupling reaction of a thiosugar, 1,4-dideoxy-1,4-epithio-D-arabinitol (3), with cyclic sulfates (8, 9, and 10), and their alpha-glucosidase inhibitory activities were examined. All these simpler analogs (5, 6, and 7) showed less inhibitory activity compared to 1a, and proved the importance of cooperative role of the polar substituents for the alpha-glucosidase inhibitory activity. A practical synthetic route to 3 starting from D-xylose is also described.
authors.affiliation: School of Pharmaceutical Sciences, Kinki University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan. muraokai@phar.kindai.ac.jp
authors.forename: Osamu
authors.initials: O
authors.lastname: Muraoka
authors.forename: Kazuya
authors.initials: K
authors.lastname: Yoshikai
authors.forename: Hideo
authors.initials: H
authors.lastname: Takahashi
authors.forename: Toshie
authors.initials: T
authors.lastname: Minematsu
authors.forename: Guangxin
authors.initials: G
authors.lastname: Lu
authors.forename: Genzoh
authors.initials: G
authors.lastname: Tanabe
authors.forename: Tao
authors.initials: T
authors.lastname: Wang
authors.forename: Hisashi
authors.initials: H
authors.lastname: Matsuda
authors.forename: Masayuki
authors.initials: M
authors.lastname: Yoshikawa
mesh_terms: D000818:Animals; D018360:Crystallography, X-Ray; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D065089:Glycoside Hydrolase Inhibitors; D013058:Mass Spectrometry; D008871:Microvilli / Q000187:drug effects / Q000201:enzymology; D013055:Spectrophotometry, Infrared; D013402:Sugar Alcohols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013431:Sulfates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D004791:Enzyme Inhibitors; D065089:Glycoside Hydrolase Inhibitors; D013402:Sugar Alcohols; D013431:Sulfates; C427963:salacinol