Synthesis of a nitrogen analogue of salacinol and its alpha-glucosidase inhibitory activity.
A nitrogen analogue 4 of the naturally occurring sulfonium ion salacinol (1), a potent alpha-glucosidase inhibitor isolated from the Ayruvedic medicine Salacia reticulata, was synthesized and its inhibitory activity against alpha-glucosidase tested. Substitution of the sulfur atom in 1 with a nitrogen reduced the activity considerably. The solid-state stereostructure of the related compound (5) was determined on the basis of single crystal X-ray measurement.
Muraoka
O
O
School of Pharmaceutical Sciences, Kinki University, Osaka, Japan. muraoka@phar,kindai.ac.jp
Ying
S
S
Yoshikai
K
K
Matsuura
Y
Y
Yamada
E
E
Minematsu
T
T
Tanabe
G
G
Matsuda
H
H
Yoshikawa
M
M
D000818:Animals; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D065089:Glycoside Hydrolase Inhibitors; D007413:Intestinal Mucosa / Q000187:drug effects / Q000201:enzymology; D051379:Mice; D008871:Microvilli / Q000187:drug effects / Q000201:enzymology; D017672:Nitrogen Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D051381:Rats; D013402:Sugar Alcohols / Q000138:chemical synthesis* / Q000494:pharmacology; D013431:Sulfates
D004791:Enzyme Inhibitors; D065089:Glycoside Hydrolase Inhibitors; D017672:Nitrogen Compounds; D013402:Sugar Alcohols; D013431:Sulfates; C427963:salacinol