Synthesis ofN-Substituted (3S,4S)- and (3R,4R)-Pyrrolidine-3,4-diols: Search for New Glycosidase Inhibitors
Publication type: Journal Article
Publication date: 2004-12-21
scimago Q2
wos Q3
SJR: 0.491
CiteScore: 3.0
Impact factor: 1.8
ISSN: 0018019X, 15222675
Catalysis
Organic Chemistry
Drug Discovery
Biochemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
N-Substituted (3S,4S)- and (3R,4R)-pyrrolidine-3,4-diols 9 and 10, respectively, were derived from (+)-L- and (-)-D-tartaric acid, respectively. Compounds 9k, 91, and 9m with the N-substituents, BnNH(CH2)(2), 4-Phc(6)H(4)CH(2)NH(CH2)(2) and 4-ClC6H4CH2NH(CH2)(2), respectively, showed modest inhibitory activities toward aD-amyloglucosidases from Aspergillus niger and from Rhizopus mold (Table 1). Unexpectedly, several (3R,4R)-pyrrolidine-3,4-diols 10 showed inhibitory activities toward alpha-D-mannosidases from almonds and from jack bean (Table 3). N-Substitution by the NH2(CH2)(2) group, i.e., 10g, led to the highest potency.
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Ysek R., Vogel P. Synthesis ofN-Substituted (3S,4S)- and (3R,4R)-Pyrrolidine-3,4-diols: Search for New Glycosidase Inhibitors // Helvetica Chimica Acta. 2004. Vol. 87. No. 12. pp. 3167-3181.
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Ysek R., Vogel P. Synthesis ofN-Substituted (3S,4S)- and (3R,4R)-Pyrrolidine-3,4-diols: Search for New Glycosidase Inhibitors // Helvetica Chimica Acta. 2004. Vol. 87. No. 12. pp. 3167-3181.
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TY - JOUR
DO - 10.1002/hlca.200490282
UR - https://doi.org/10.1002/hlca.200490282
TI - Synthesis ofN-Substituted (3S,4S)- and (3R,4R)-Pyrrolidine-3,4-diols: Search for New Glycosidase Inhibitors
T2 - Helvetica Chimica Acta
AU - Ysek, Robert
AU - Vogel, P.
PY - 2004
DA - 2004/12/21
PB - Wiley
SP - 3167-3181
IS - 12
VL - 87
SN - 0018-019X
SN - 1522-2675
ER -
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BibTex (up to 50 authors)
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@article{2004_Ysek,
author = {Robert Ysek and P. Vogel},
title = {Synthesis ofN-Substituted (3S,4S)- and (3R,4R)-Pyrrolidine-3,4-diols: Search for New Glycosidase Inhibitors},
journal = {Helvetica Chimica Acta},
year = {2004},
volume = {87},
publisher = {Wiley},
month = {dec},
url = {https://doi.org/10.1002/hlca.200490282},
number = {12},
pages = {3167--3181},
doi = {10.1002/hlca.200490282}
}
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MLA
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Ysek, Robert, and P. Vogel. “Synthesis ofN-Substituted (3S,4S)- and (3R,4R)-Pyrrolidine-3,4-diols: Search for New Glycosidase Inhibitors.” Helvetica Chimica Acta, vol. 87, no. 12, Dec. 2004, pp. 3167-3181. https://doi.org/10.1002/hlca.200490282.