Fluorinated Radicamine A and B: Synthesis and Glycosidase Inhibition

Yi Xian Li; Ren Iwaki; Atsushi Kato; Yue Mei Jia; George W.J. Fleet; Xuan Zhao; Min Xiao; Chu Yi Yu

doi:10.1002/ejoc.201501453

Fluorinated Radicamine A and B: Synthesis and Glycosidase Inhibition

Yi Xian Li, Ren Iwaki, Atsushi Kato^*, Yue Mei Jia, George W.J. Fleet, Xuan Zhao, Min Xiao, Chu Yi Yu

^*Corresponding author for this work

Hospital Pharmacy

Research output: Contribution to journal › Article › peer-review

21 Scopus citations

Abstract

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. Fluorinated derivatives of radicamine A and B have been synthesized from D-arabinose-derived cyclic nitrone. Structure-activity relationship studies revealed that glycosidase inhibition of these fluorinated derivatives was significantly influenced by the position of the fluorine atom.

Original language	English
Pages (from-to)	1429-1438
Number of pages	10
Journal	European Journal of Organic Chemistry
Volume	2016
Issue number	7
DOIs	https://doi.org/10.1002/ejoc.201501453
State	Published - 2016/03/01

Keywords

Azasugars
Drug design
Fluorine
Iminosugar
Inhibitors
Structure-activity relationships

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.201501453

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title = "Fluorinated Radicamine A and B: Synthesis and Glycosidase Inhibition",

abstract = "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. Fluorinated derivatives of radicamine A and B have been synthesized from D-arabinose-derived cyclic nitrone. Structure-activity relationship studies revealed that glycosidase inhibition of these fluorinated derivatives was significantly influenced by the position of the fluorine atom.",

keywords = "Azasugars, Drug design, Fluorine, Iminosugar, Inhibitors, Structure-activity relationships",

author = "Li, {Yi Xian} and Ren Iwaki and Atsushi Kato and Jia, {Yue Mei} and Fleet, {George W.J.} and Xuan Zhao and Min Xiao and Yu, {Chu Yi}",

note = "Publisher Copyright: Copyright {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

year = "2016",

month = mar,

day = "1",

doi = "10.1002/ejoc.201501453",

language = "英語",

volume = "2016",

pages = "1429--1438",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

number = "7",

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TY - JOUR

T1 - Fluorinated Radicamine A and B

T2 - Synthesis and Glycosidase Inhibition

AU - Li, Yi Xian

AU - Iwaki, Ren

AU - Kato, Atsushi

AU - Jia, Yue Mei

AU - Fleet, George W.J.

AU - Zhao, Xuan

AU - Xiao, Min

AU - Yu, Chu Yi

PY - 2016/3/1

Y1 - 2016/3/1

N2 - 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. Fluorinated derivatives of radicamine A and B have been synthesized from D-arabinose-derived cyclic nitrone. Structure-activity relationship studies revealed that glycosidase inhibition of these fluorinated derivatives was significantly influenced by the position of the fluorine atom.

AB - 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. Fluorinated derivatives of radicamine A and B have been synthesized from D-arabinose-derived cyclic nitrone. Structure-activity relationship studies revealed that glycosidase inhibition of these fluorinated derivatives was significantly influenced by the position of the fluorine atom.

KW - Azasugars

KW - Drug design

KW - Fluorine

KW - Iminosugar

KW - Inhibitors

KW - Structure-activity relationships

UR - http://www.scopus.com/inward/record.url?scp=84959928619&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201501453

DO - 10.1002/ejoc.201501453

M3 - 学術論文

AN - SCOPUS:84959928619

SN - 1434-193X

VL - 2016

SP - 1429

EP - 1438

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 7

ER -

Fluorinated Radicamine A and B: Synthesis and Glycosidase Inhibition

Abstract

Keywords

ASJC Scopus subject areas

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