Solid-phase synthesis of 3,7-disubstituted perhydro-1,4-diazepine-2,5-amino acids from amino acids and β-amino acids

被引：23

作者：

Giovannoni, J ^{[1
]}

Subra, G ^{[1
]}

Amblard, M ^{[1
]}

Martinez, J ^{[1
]}

机构：

[1] Univ Montpellier 1, CNRS, Fac Pharm, LAPP,UMR5810, F-34060 Montpellier, France

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 32期

关键词：

diazepine; mimotopes crowns; backbone amide linker;

D O I：

10.1016/S0040-4039(01)00972-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report here the synthesis of 3,7-disubstituted perhydro- 1,4-diazepine-2,5- diones from amino acids and beta -amino acids using a backbone amide linker (DAL) as a cis-configuration inductor. We have optimized each steps of the synthesis on solid Support using Mimotopes crowns. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：5389 / 5392

页数：4

共 10 条

[1]

BRAY AM, 1995, TETRAHEDRON LETT, V36, P5081

[2] A GENERAL AND EXPEDIENT METHOD FOR THE SOLID-PHASE SYNTHESIS OF 1,4-BENZODIAZEPINE DERIVATIVES [J].

BUNIN, BA ;

ELLMAN, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (27) :10997-10998

[3] Solid-phase synthesis of diketopiperazines, useful scaffolds for combinatorial chemistry [J].

del Fresno, M ;

Alsina, J ;

Royo, M ;

Barany, G ;

Albericio, F .

TETRAHEDRON LETTERS, 1998, 39 (17) :2639-2642

[4] USE OF PEPTIDE-SYNTHESIS TO PROBE VIRAL-ANTIGENS FOR EPITOPES TO A RESOLUTION OF A SINGLE AMINO-ACID [J].

GEYSEN, HM ;

MELOEN, RH ;

BARTELING, SJ .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA-BIOLOGICAL SCIENCES, 1984, 81 (13) :3998-4002

[5] APPLICATIONS OF COMBINATORIAL TECHNOLOGIES TO DRUG DISCOVERY .2. COMBINATORIAL ORGANIC-SYNTHESIS, LIBRARY SCREENING STRATEGIES, AND FUTURE-DIRECTIONS [J].

GORDON, EM ;

BARRETT, RW ;

DOWER, WJ ;

FODOR, SPA ;

GALLOP, MA .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (10) :1385-1401

[6] Solid-phase synthesis via N-terminal attachment to the 2-chlorotrityl resin [J].

Hoekstra, WJ ;

Greco, MN ;

Yabut, SC ;

Hulshizer, BL ;

Maryanoff, BE .

TETRAHEDRON LETTERS, 1997, 38 (15) :2629-2632

[7] Backbone Amide Linker (BAL) strategy for solid-phase synthesis of C-terminal-modified and cyclic peptides [J].

Jensen, KJ ;

Alsina, J ;

Songster, MF ;

Vágner, J ;

Albericio, F ;

Barany, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (22) :5441-5452

[8] Polymer-supported synthesis of diverse perhydro-1,4-diazepine-2,5-diones [J].

Krchnak, V ;

Weichsel, AS .

TETRAHEDRON LETTERS, 1997, 38 (42) :7299-7302

[9] Solid phase synthesis of 1,3,4,7-tetrasubstituted perhydro-1,4-diazepine-2,5-diones [J].

Nefzi, A ;

Ostresh, JM ;

Houghten, RA .

TETRAHEDRON LETTERS, 1997, 38 (28) :4943-4946

[10] COMBINATORIAL SYNTHESIS - THE DESIGN OF COMPOUND LIBRARIES AND THEIR APPLICATION TO DRUG DISCOVERY [J].

TERRETT, NK ;

GARDNER, M ;

GORDON, DW ;

KOBYLECKI, RJ ;

STEELE, J .

TETRAHEDRON, 1995, 51 (30) :8135-8173

← 1 →