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N-hydroxyethyl-piperidine and -pyrrolidine homoazasugars: preparation and evaluation of glycosidase inhibitory activity.

Abstract：

:An efficient and practical strategy for the synthesis of N-hydroxyethyl-1-deoxy-homonojirimycins 4 and 5 and N-hydroxyethyl-pyrrolidine homoazasugars 6 and 7 with full stereocontrol is being reported. The key step involved is the intermolecular Michael addition of benzylamine to D-glucose derived alpha,beta-unsaturated ester 8 followed by N-alkylation with ethyl bromoacetate. Reduction with LAH, acetylation, hydrogenation and protection with -Cbz group afforded compounds 14a and 14b. Removal of 1,2-acetonide functionality, hydrogenation and deacetylation afforded N-hydroxyethyl-D-gluco-1-deoxyhomonojirimycin (4) and N-hydroxyethyl-L-ido-1-deoxyhomonojirimycin (5), respectively. Compounds 14a and 14b on acetylation followed by removal of 1,2-acetonide functionality, sodium metaperiodate oxidation, hydrogenation and deacetylation gave 1,4,5-trideoxy-1,4-imino-N-hydroxyethyl-D-arabino-hexitol (6) and 1,4,5-trideoxy-1,4-imino-N-hydroxyethyl-L-xylo-hexitol (7), respectively. The glycosidase inhibition activity of compounds 4, 5, 6, 7, 16a and 16b was evaluated using sweet almond seed as a rich source of different glycosidases.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Dhavale DD,Matin MM,Sharma T,Sabharwal SG

doi

10.1016/s0968-0896(03)00231-1

subject

Has Abstract

pub_date

2003-07-31 00:00:00

pages

3295-305

issue

15

eissn

0968-0896

issn

1464-3391

pii

S0968089603002311

journal_volume

11

pub_type

杂志文章

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