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Fluorinated Radicamine A and B: Synthesis and Glycosidase Inhibition
Author(s) -
Li YiXian,
Iwaki Ren,
Kato Atsushi,
Jia YueMei,
Fleet George W. J.,
Zhao Xuan,
Xiao Min,
Yu ChuYi
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501453
Subject(s) - chemistry , glycoside hydrolase , stereochemistry , ring (chemistry) , fluorine , nitrone , arabinose , enzyme , organic chemistry , catalysis , fermentation , cycloaddition , xylose
Fluorinated derivatives of radicamine A and radicamine B have been synthesized from D ‐arabinose‐derived cyclic nitrone. Structure–activity relationship studies showed that glycosidase inhibition of these fluorinated derivatives was significantly influenced by the position of the fluorine atom. C‐7 or C‐11 fluorination of the aromatic ring decreased α‐glucosidase inhibition of the derivatives, whereas C‐8 or C‐10 fluorination preserved glycosidase inhibitory activities.