Synthesis of constrained L-phenylalanine derivatives incorporating a benzazepinone or an azepinone ring as VCAM/VLA-4 antagonists

被引：8

作者：

Sidduri, A ^{[1
]}

Lou, JP ^{[1
]}

Campbell, R ^{[1
]}

Rowan, K ^{[1
]}

Tilley, JW ^{[1
]}

机构：

[1] Hoffmann La Roche Inc, Roche Res Ctr, Nutley, NJ 07110 USA

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 50期

关键词：

D O I：

10.1016/S0040-4039(01)01926-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel constrained L-phenylalanine derivatives incorporating a benzazepinone or an azepinone ring were synthesized in 13 and 8 steps, respectively, employing a key base-catalyzed intramolecular cyclization reaction. The product, 2, was comparable in potency in a VCAM/VLA-4 ELISA assay to the corresponding unconstrained analog I suggesting that cyclization favored the bioactive conformation. However, compound 4 was 100-fold less potent than the unconstrained analog 3. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：8757 / 8760

页数：4

共 5 条

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