title: Synthesis of a salacinol analogue and its alpha-glucosidase inhibitory activity.
abstract: OBJECTIVE
  To investigate more efficient synthetic method of the nitrogen analogue 4 of salacinol (1) for searching new antidiabetic agents.
  
  
  METHODS
  The synthesis of the key intermediate 2, 4-O-isopropylidene-L-erythritol 1,3-cyclic sulfate (2a) was accomplished by modification of reports from D-glucose via seven steps in much more less expensive. Using this method, an efficient synthesis of 4 was carried out. The glycosidase inhibitory activity of 4 was tested for the intestinal alpha-glucosidase in vitro and compared with that of salacinol.
  
  
  RESULTS
  A nitrogen analogue 4 of salacinol (1) was synthesized by the coupling reaction between the cyclic sulfate 2a and an azasugar 3b.
  
  
  CONCLUSIONS
  Substitution of the sulfur atom in 1 with a nitrogen reduced the activity considerably.
authors.affiliation: Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, China. shaoy@cde.org.cn
authors.forename: Ying
authors.initials: Y
authors.lastname: Shao
authors.forename: Muraoka
authors.initials: M
authors.lastname: Osamu
authors.forename: Yoshikai
authors.initials: Y
authors.lastname: Kazuya
authors.forename: Matsuura
authors.initials: M
authors.lastname: Yoshiharu
authors.forename: Yamada
authors.initials: Y
authors.lastname: Eriko
authors.forename: Minematsu
authors.initials: M
authors.lastname: Toshie
authors.forename: Tanabe
authors.initials: T
authors.lastname: Genzoh
authors.forename: Matsuda
authors.initials: M
authors.lastname: Hisashi
authors.forename: Yoshikawa
authors.initials: Y
authors.lastname: Masayuki
authors.forename: Qi-dong
authors.initials: QD
authors.lastname: You
mesh_terms: D000818:Animals; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D065089:Glycoside Hydrolase Inhibitors; D007413:Intestinal Mucosa / Q000187:drug effects / Q000201:enzymology; D015394:Molecular Structure; D017672:Nitrogen Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D051381:Rats; D013329:Structure-Activity Relationship; D013402:Sugar Alcohols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013431:Sulfates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000520:alpha-Glucosidases / Q000378:metabolism
chemical_list: D004791:Enzyme Inhibitors; D065089:Glycoside Hydrolase Inhibitors; D017672:Nitrogen Compounds; D013402:Sugar Alcohols; D013431:Sulfates; C427963:salacinol; D000520:alpha-Glucosidases