Bicyclic isoureas derived from 1-deoxynojirimycin are potent inhibitors of β-glucocerebrosidase

Alen Sevšek; Maša Čelan; Bibi Erjavec; Linda Quarles van Ufford; Javier Sastre Toraño; Ed E Moret; Roland J Pieters; Nathaniel I Martin

doi:10.1039/c6ob01735e

Bicyclic isoureas derived from 1-deoxynojirimycin are potent inhibitors of β-glucocerebrosidase

Alen Sevšek, Maša Čelan, Bibi Erjavec, Linda Quarles van Ufford, Javier Sastre Toraño, Ed E Moret, Roland J Pieters, Nathaniel I Martin

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

Abstract

A series of bicyclic isourea derivatives were prepared from 1-deoxynojirimycin using a concise synthetic protocol proceeding via a guanidino intermediate. Inhibition assays with a panel of glycosidases revealed that these deoxynojirimycin-derived bicyclic isoureas display very potent inhibition against human recombinant β-glucocerebrosidase with IC50 values in the low nanomolar range.

Original language	English
Pages (from-to)	8670-3
Number of pages	4
Journal	Organic & Biomolecular Chemistry
Volume	14
Issue number	37
DOIs	https://doi.org/10.1039/c6ob01735e
Publication status	Published - 2016

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BicyclicFinal published version, 791 KBLicence: Taverne

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abstract = "A series of bicyclic isourea derivatives were prepared from 1-deoxynojirimycin using a concise synthetic protocol proceeding via a guanidino intermediate. Inhibition assays with a panel of glycosidases revealed that these deoxynojirimycin-derived bicyclic isoureas display very potent inhibition against human recombinant β-glucocerebrosidase with IC50 values in the low nanomolar range.",

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doi = "10.1039/c6ob01735e",

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T1 - Bicyclic isoureas derived from 1-deoxynojirimycin are potent inhibitors of β-glucocerebrosidase

AU - Sevšek, Alen

AU - Čelan, Maša

AU - Erjavec, Bibi

AU - Quarles van Ufford, Linda

AU - Sastre Toraño, Javier

AU - Moret, Ed E

AU - Pieters, Roland J

AU - Martin, Nathaniel I

PY - 2016

Y1 - 2016

N2 - A series of bicyclic isourea derivatives were prepared from 1-deoxynojirimycin using a concise synthetic protocol proceeding via a guanidino intermediate. Inhibition assays with a panel of glycosidases revealed that these deoxynojirimycin-derived bicyclic isoureas display very potent inhibition against human recombinant β-glucocerebrosidase with IC50 values in the low nanomolar range.

AB - A series of bicyclic isourea derivatives were prepared from 1-deoxynojirimycin using a concise synthetic protocol proceeding via a guanidino intermediate. Inhibition assays with a panel of glycosidases revealed that these deoxynojirimycin-derived bicyclic isoureas display very potent inhibition against human recombinant β-glucocerebrosidase with IC50 values in the low nanomolar range.

U2 - 10.1039/c6ob01735e

DO - 10.1039/c6ob01735e

M3 - Article

C2 - 27604065

SN - 1477-0520

VL - 14

SP - 8670

EP - 8673

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 37

ER -

Bicyclic isoureas derived from 1-deoxynojirimycin are potent inhibitors of β-glucocerebrosidase

Abstract

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