The synthesis of β-strand mimetic templates via regioselective 1,3-dipolar cycloaddition with vinylsulfone

被引：26

作者：

Fuchi, N

Doi, T

Harada, T

Urban, J

Cao, BL

Kahn, M

Takahashi, T

机构：

[1] Tokyo Inst Technol, Grad Sch Sci & Engn, Dept Appl Chem, Tokyo 1528552, Japan

[2] Molecumet Ltd, Bellevue, WA 98005 USA

[3] Univ Washington, Dept Pathobiol, Seattle, WA 98195 USA

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 07期

关键词：

1,3-dipolar cycloaddition; vinyl sulfone; peptidomimetics; serine protease inhibitor;

D O I：

10.1016/S0040-4039(00)02229-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed a practical synthetic route to constrained P-strand mimetic templates by regioselective 1,3-dipolar cycloaddition of azomethine imines with vinyl sulfone. A small library of P-strand mimetic templates was generated which include potent and selective inhibitors of serine proteases. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：1305 / 1308

页数：4

相关论文

共 11 条

[1] Secondary structure peptide mimetics:: Design, synthesis, and evaluation of β-strand mimetic thrombin inhibitors [J].

Boatman, PD ;

Ogbu, CO ;

Eguchi, M ;

Kim, HO ;

Nakanishi, H ;

Cao, BL ;

Shea, JP ;

Kahn, M .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (08) :1367-1375

[2]

Bode W., 1992, EUR J BIOCHEM, V204, P2554

[3] SELECTIVITY IN CYCLO-ADDITIONS .11. CYCLO-ADDITIONS OF NITRILE OXIDES TO METHYL STYRYL SULFIDES, SULFOXIDES AND SULFONES - REGIOCHEMISTRY [J].

CARAMELLA, P ;

ALBINI, E ;

BANDIERA, T ;

CODA, AC ;

GRUNANGER, P ;

ALBINI, FM .

TETRAHEDRON, 1983, 39 (04) :689-699

[4] Design and synthesis of conformationally constrained amino acids as versatile scaffolds and peptide mimetics [J].

Hanessian, S ;

McNaughtonSmith, G ;

Lombart, HG ;

Lubell, WD .

TETRAHEDRON, 1997, 53 (38) :12789-12854

[5] 1,3-DIPOLAR CYCLO-ADDITION REACTIONS OF PYRAZOLIDINIUM YLIDES WITH VINYL SULFONES - A REGIOSELECTIVE SYNTHESIS OF BICYCLIC PYRAZOLIDINONE ANTIBACTERIAL AGENTS [J].

JUNGHEIM, LN ;

BARNETT, CJ ;

GRAY, JE ;

HORCHER, LH ;

SHEPHERD, TA ;

SIGMUND, SK .

TETRAHEDRON, 1988, 44 (11) :3119-3126

[6]

KAHN M, 1993, SYNLETT, P821

[7] D-PHE-PRO-ARGCH2C1-A SELECTIVE AFFINITY LABEL FOR THROMBIN [J].

KETTNER, C ;

SHAW, E .

THROMBOSIS RESEARCH, 1979, 14 (06) :969-973

[8] REGIO-SELECTIVE AND STEREO-SELECTIVE SYNTHESIS OF BETA-SULPHONYL-ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS VIA AN IODOSULFONYLATION DEHYDROIODINATION REACTION [J].

NAJERA, C ;

BALDO, B ;

YUS, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (05) :1029-1032

[9] Highly efficient and versatile synthesis of libraries of constrained β-strand mimetics [J].

Ogbu, CO ;

Qabar, MN ;

Boatman, PD ;

Urban, J ;

Meara, JP ;

Ferguson, MD ;

Tulinsky, J ;

Lum, C ;

Babu, S ;

Blaskovich, MA ;

Nakanishi, H ;

Ruan, FQ ;

Cao, BL ;

Minarik, R ;

Little, T ;

Nelson, S ;

Nguyen, M ;

Gall, A ;

Kahn, M .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (17) :2321-2326

[10] REGIOSELECTIVITY OF 1,3-DIPOLAR CYCLO-ADDITION REACTIONS OF NITRILIMINES WITH ARYL VINYL SULFONES [J].

SHIMIZU, T ;

HAYASHI, Y ;

MIKI, M ;

TERAMURA, K .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (06) :904-907