Synthesis of 4-amino-3-oxo-tetrahydroazepino[3,4-b]indoles:: new conformationally constrained Trp analogs

被引：24
|
作者：
Pulka, Karolina
Feytens, Debby
Van den Eynde, Isabelle
De Wachter, Rien
Kosson, Piotr
Misicka, Aleksandra
Lipkowski, Andrzej
Chung, Nga N.
Schiller, Peter W.
Tourwe, Dirk
机构：
[1] Vrije Univ Brussels, Dept Organ Chem, B-1050 Brussels, Belgium
[2] Warsaw Univ, Dept Chem, PL-02093 Warsaw, Poland
[3] Polish Acad Sci, Med Res Ctr, PL-02106 Warsaw, Poland
[4] Clin Res Inst Montreal, Lab Chem Biol & Peptide Res, Montreal, PQ H2W 1R7, Canada
来源：
TETRAHEDRON | 2007年 / 63卷 / 06期
关键词：
D O I：
10.1016/j.tet.2006.11.069
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis of tryptophan analogs is reported in which the conformation has been constrained by formation of a sevenmembered lactam. Boc-protected 2'-formyl tryptophan was obtained by SeO2 oxidation of Boc-tetrahydro-beta-carboline-3-carboxylic acid. Reductive amination was performed with a variety of amines and amino acid esters using sodium cyanoborohydride, followed by ring closure to the target compounds. The constrained Trp derivative has been incorporated into the endomorphin-1 opioid peptide sequence to probe the bioactive conformation. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1459 / 1466
页数：8
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