Stereoselective synthesis of beta-1-C-substituted 1,4-dideoxy-1,4-imino-D-galactitols and evaluation as UDP-galactopyranose mutase inhibitors.
The synthesis of 1-C-substituted 1,4-dideoxy-1,4-imino-D-galactitols involving nitrone umpolung is described. The SmI(2)-induced key coupling proved highly stereoselective in favor of the beta-C-substituted products bearing a three-carbon chain at the pseudoanomeric position. Pyrrolidines 9 and 10, as well as the bicyclic compounds 8 and 11, exhibit weak inhibition of the activity of the UDP-galactopyranose mutase from Escherichia coli.
Desvergnes
Stéphanie
S
Département de Chimie Moléculaire (SERCO) UMR-5250, ICMG FR-2607, CNRS--Université Joseph Fourier, BP 53, F-38041 Grenoble Cedex 9, France.
Desvergnes
Valérie
V
Martin
Olivier R
OR
Itoh
Kenji
K
Liu
Hung-wen
HW
Py
Sandrine
S
D001643:Bridged Bicyclo Compounds / Q000737:chemistry / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology*; D004926:Escherichia coli / Q000201:enzymology; D004376:Galactitol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology*; D019751:Intramolecular Transferases / Q000037:antagonists & inhibitors*; D011759:Pyrrolidines / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D001643:Bridged Bicyclo Compounds; D004791:Enzyme Inhibitors; D011759:Pyrrolidines; D004376:Galactitol; D019751:Intramolecular Transferases; C098051:UDP-galactopyranose mutase