Synthesis of benzyl (6S)-1,3-dichloro-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrazine-6-carboxylic ester, a new conformationally constrained peptidomimetic derivative

被引：9

作者：

Gloanec, P

Hervé, Y

Brémand, N

Lecouvé, JP

Bréard, F

De Nanteuil, G

机构：

[1] Inst Rech Servier, F-92150 Suresnes, France

[2] Oril Ind, F-76210 Bolbec, France

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 19期

关键词：

peptidomimetic; pyroglutamic acid; 4-oxo-4,6,7,8-tetra-hydro-pyrrolo[1,2-a]pyrazine;

D O I：

10.1016/S0040-4039(02)00574-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe the synthesis of benzyl (6S)-1,3-dichloro-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-alpha]pyrazine-6-carboxylic ester, a new conformationally constrained peptidomimetic derivative. This compound is prepared in seven steps from (S)-pyroglutamic acid as starting material. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：3499 / 3501

页数：3

共 15 条

[1]

ADANG AEP, 1994, RECL TRAV CHIM PAY B, V113, P63

[2] DESIGN OF ORALLY-ACTIVE, NONPEPTIDIC INHIBITORS OF HUMAN-LEUKOCYTE ELASTASE [J].

BROWN, FJ ;

ANDISIK, DW ;

BERNSTEIN, PR ;

BRYANT, CB ;

CECCARELLI, C ;

DAMEWOOD, JR ;

WOOLSON, SA ;

EDWARDS, PD ;

EARLEY, RA ;

FEENEY, S ;

GREEN, RC ;

GOMES, B ;

KOSMIDER, BJ ;

KRELL, RD ;

SHAW, A ;

STEELMAN, GB ;

THOMAS, RN ;

VACEK, EP ;

VEALE, CA ;

TUTHILL, PA ;

WARNER, P ;

WILLIAMS, JC ;

WOLANIN, DJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (09) :1259-1261

[3]

DENANTEUIL G, Patent No. 1069132

[4] AMINO-ACIDS .9. REACTIONS OF 5-OXOPROLINE DERIVATIVES WITH PHOSPHORUS-PENTACHLORIDE - SYNTHESIS OF CHLORO-PYRROLE-2-CARBOXYLIC ACID-DERIVATIVES [J].

EFFENBERGER, F ;

MULLER, W ;

ISAK, H .

CHEMISCHE BERICHTE-RECUEIL, 1987, 120 (01) :45-54

[5]

GANTE J, 1994, ANGEW CHEM INT EDIT, V33, P1699, DOI 10.1002/anie.199416991

[6]

GIANIS A, 1993, ANGEW CHEM INT EDIT, V33, P1244

[7] 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

[8] Synthesis of conformationally constrained analogues of (R)-2-amino-7-phosphonoheptanoic acid [J].

Langlois, N ;

RojasRousseau, A ;

Decavallas, O .

TETRAHEDRON-ASYMMETRY, 1996, 7 (04) :1095-1100

[9] A SHORT SYNTHESIS OF C-2 SYMMETRICAL (2S, 5S) PYRROLIDINE-2,5 DICARBOXYLIC-ACID, A CONSTITUENT OF RED ALGA SCHIZYMENIA-DUBYI [J].

LANGLOIS, N ;

ROJAS, A .

TETRAHEDRON, 1993, 49 (01) :77-82

[10] CONCEPTS AND PROGRESS IN THE DEVELOPMENT OF PEPTIDE MIMETICS [J].

OLSON, GL ;

BOLIN, DR ;

BONNER, MP ;

BOS, M ;

COOK, CM ;

FRY, DC ;

GRAVES, BJ ;

HATADA, M ;

HILL, DE ;

KAHN, M ;

MADISON, VS ;

RUSIECKI, VK ;

SARABU, R ;

SEPINWALL, J ;

VINCENT, GP ;

VOSS, ME .

JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (21) :3039-3049

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