Synthesis of monofluorinated isofagomine analogues and evaluation as glycosidase inhibitors

Yi Yang; Feng Zheng; Mikael Bols; Lavinia G Marinescu; Feng-Ling Qing

Synthesis of monofluorinated isofagomine analogues and evaluation as glycosidase inhibitors

Yi Yang, Feng Zheng, Mikael Bols, Lavinia G Marinescu, Feng-Ling Qing

Department of Chemistry

18 Citations (Scopus)

Abstract

The straightforward synthesis of monofluorinated isofagomine analogues 1-3 was described. The synthetic strategy featured that the chiral carbon center bearing fluorine atom was constructed stereoselectively via silicon-induced Reformatskii-Claisen rearrangement of allyl bromofluoroacetate. These compounds were tested for inhibition of five glycosidases. The 3S,4R,5R isomer 3 has been found to be a potent inhibitor against β-glucosidase from almonds with K_i value of 11.9 μM.

Original language	English
Journal	Journal of Fluorine Chemistry
Volume	132
Pages (from-to)	838–845
ISSN	0022-1139
Publication status	Published - Oct 2011

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title = "Synthesis of monofluorinated isofagomine analogues and evaluation as glycosidase inhibitors",

abstract = "The straightforward synthesis of monofluorinated isofagomine analogues 1-3 was described. The synthetic strategy featured that the chiral carbon center bearing fluorine atom was constructed stereoselectively via silicon-induced Reformatskii-Claisen rearrangement of allyl bromofluoroacetate. These compounds were tested for inhibition of five glycosidases. The 3S,4R,5R isomer 3 has been found to be a potent inhibitor against β-glucosidase from almonds with Ki value of 11.9 μM.",

author = "Yi Yang and Feng Zheng and Mikael Bols and Marinescu, {Lavinia G} and Feng-Ling Qing",

year = "2011",

month = oct,

language = "English",

volume = "132",

pages = "838–845",

journal = "Journal of Fluorine Chemistry",

issn = "0022-1139",

publisher = "Elsevier",

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TY - JOUR

T1 - Synthesis of monofluorinated isofagomine analogues and evaluation as glycosidase inhibitors

AU - Yang, Yi

AU - Zheng, Feng

AU - Bols, Mikael

AU - Marinescu, Lavinia G

AU - Qing, Feng-Ling

PY - 2011/10

Y1 - 2011/10

N2 - The straightforward synthesis of monofluorinated isofagomine analogues 1-3 was described. The synthetic strategy featured that the chiral carbon center bearing fluorine atom was constructed stereoselectively via silicon-induced Reformatskii-Claisen rearrangement of allyl bromofluoroacetate. These compounds were tested for inhibition of five glycosidases. The 3S,4R,5R isomer 3 has been found to be a potent inhibitor against β-glucosidase from almonds with Ki value of 11.9 μM.

AB - The straightforward synthesis of monofluorinated isofagomine analogues 1-3 was described. The synthetic strategy featured that the chiral carbon center bearing fluorine atom was constructed stereoselectively via silicon-induced Reformatskii-Claisen rearrangement of allyl bromofluoroacetate. These compounds were tested for inhibition of five glycosidases. The 3S,4R,5R isomer 3 has been found to be a potent inhibitor against β-glucosidase from almonds with Ki value of 11.9 μM.

M3 - Journal article

SN - 0022-1139

VL - 132

SP - 838

EP - 845

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

ER -

Synthesis of monofluorinated isofagomine analogues and evaluation as glycosidase inhibitors

Abstract

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