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Synthesis of new six- and seven-membered 1-N-iminosugars as promising glycosidase inhibitors.

Abstract：

:New six- and seven-membered 1-N-iminosugars were prepared from d-glucose by the stereoselective Michael addition of nitromethane to d-glucose derived α,β-unsaturated ester A followed by one pot reduction of nitro/ester functionality and subsequent amine protection to get N-Cbz protected aminol 6. Hydrolysis of 1,2-acetonide and reductive aminocyclization gave seven membered 1-N-iminosugar 5b. While, hydrolysis of 1,2-acetonide followed by NaIO(4) oxidative cleavage and hydrogenation using 10% Pd(OH)(2)/C, H(2) gave six membered 1-N-iminosugar 4a; the hydrogenation using 10% Pd/C-H(2) however, gave N-methyl substituted 1-N-iminosugar 4b. The hydrochloride salts of 4a/4b and 5b were found to be specific α-galactosidase and moderate α-glucosidae inhibitors, respectively, in micro molar range.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Jabgunde AM,Kalamkar NB,Chavan ST,Sabharwal SG,Dhavale DD

doi

10.1016/j.bmc.2011.07.059

subject

Has Abstract

pub_date

2011-10-01 00:00:00

pages

5912-5

issue

19

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(11)00621-3

journal_volume

19

pub_type

杂志文章

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