exo-imino to endo-iminocyclitol rearrangement.: A general route to five-membered antiviral azasugars

被引：28

作者：

Moriarty, Robert M. ^{[1
]}

Mitan, Carmen I.

Branza-Nichita, Norica

Phares, Kenneth R.

Parrish, Damon

机构：

[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA

[2] Romanian Acad, Inst Biochem, Bucharest 77700, Romania

[3] United Therapeut Corp Res, Res Triangle Pk, NC 27709 USA

[4] USN, Res Lab, Struct Matter Lab, Dept Navy, Washington, DC 20375 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 16期

关键词：

D O I：

10.1021/ol061071r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile synthesis is reported for five-membered iminocyclitols which allows for variation in stereochemistry at all the chiral centers, diverse C-1- and N-substitution, and the potential for a three-component combinatorial process. The key step is inversion at the C-4 stereocenter (L-lyxo sugar -> D-ribono azasugar). The exo-imino to endo-iminocyclitol process was extended to the D-lyxo and the D- and L-hexose series. Some analogues were found to be more potent than N-butyl DNJ and N-nonyl DNJ in antiviral activity.

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页码：3465 / 3467

页数：3

相关论文

共 36 条

[1] CHANGE IN SPECIFICITY OF GLYCOSIDASE INHIBITION BY N-ALKYLATION OF AMINO-SUGARS [J].

ALDAHER, S ;

FLEET, G ;

NAMGOONG, SK ;

WINCHESTER, B .

BIOCHEMICAL JOURNAL, 1989, 258 (02) :613-615

[2] RULES FOR RING-CLOSURE [J].

BALDWIN, JE .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :734-736

[3] SYNTHESIS FROM D-LYXONOLACTONE OF 1,4-DIDEOXY-1,4-IMINO-L-ARABINITOL, A GLUCOSIDASE INHIBITOR WITH INVITRO ANTIVIRAL ACTIVITY [J].

BEHLING, JR ;

CAMPBELL, AL ;

BABIAK, KA ;

NG, JS ;

MEDICH, J ;

FARID, P ;

FLEET, GWJ .

TETRAHEDRON, 1993, 49 (16) :3359-3366

[4] SECRETION OF HUMAN HEPATITIS-B VIRUS IS INHIBITED BY THE IMINO SUGAR N-BUTYLDEOXYNOJIRIMYCIN [J].

BLOCK, TM ;

LU, XY ;

PLATT, FM ;

FOSTER, GR ;

GERLICH, WH ;

BLUMBERG, BS ;

DWEK, RA .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1994, 91 (06) :2235-2239

[5] Design and synthesis of iminosugar-based inhibitors of glucosylceramide synthase: the search for new therapeutic agents against Gaucher disease [J].

Boucheron, C ;

Desvergnes, V ;

Compain, P ;

Martin, OR ;

Lavi, A ;

Mackeen, M ;

Wormald, M ;

Dwek, R ;

Butters, TD .

TETRAHEDRON-ASYMMETRY, 2005, 16 (10) :1747-1756

[6] Antiviral effect of N-butyldeoxynojirimycin against bovine viral diarrhea virus correlates with misfolding of E2 envelope proteins and impairment of their association into E1-E2 heterodimers [J].

Branza-Nichita, N ;

Durantel, D ;

Carrouée-Durantel, S ;

Dwek, RA ;

Zitzmann, N .

JOURNAL OF VIROLOGY, 2001, 75 (08) :3527-3536

[7] Glyco- and peptidomimetics from three-component Joullie-Ugi coupling show selective antiviral activity [J].

Chapman, TM ;

Davies, IG ;

Gu, B ;

Block, TM ;

Scopes, DIC ;

Hay, PA ;

Courtney, SM ;

McNeill, LA ;

Schofield, CJ ;

Davis, BG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (02) :506-507

[8]

DIBELLO IC, 1989, BIOCHEM J, V259, P855

[9] Effects of interferon, ribavirin, and iminosugar derivatives on cells persistently infected with noncytopathic bovine viral diarrhea virus [J].

Durantel, D ;

Carrouée-Durantel, S ;

Branza-Nichita, N ;

Dwek, RA ;

Zitzmann, N .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2004, 48 (02) :497-504

[10] Study of the mechanism of antiviral action of iminosugar derivatives against bovine viral diarrhea virus [J].

Durantel, D ;

Branza-Nichita, N ;

Carrouée-Durantel, S ;

Butters, TD ;

Dwek, RA ;

Zitzmann, N .

JOURNAL OF VIROLOGY, 2001, 75 (19) :8987-8998

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