From cyclic dehydrodipeptides to uncommon acyclic peptide mimetics

被引：7
作者：
Francisco Gonzalez, Juan [1 ]
de la Cuesta, Elena [1 ]
Avendano, Carmen [1 ]
机构：
[1] Univ Complutense Madrid, Fac Farm, Dept Quim Organ & Farmaceut, E-28040 Madrid, Spain
来源：
TETRAHEDRON LETTERS | 2006年 / 47卷 / 38期
关键词：
D O I：
10.1016/j.tetlet.2006.07.095
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
1-Acetyl-3 -arylmethylene-2,5-piperazinediones gave N-3-arylpyruvylamino esters by acid-promoted alcoholysis under thermal conditions or microwave irradiation. Compounds obtained from 1-acetyl-3-(o-nitro)arylmethylene-2,5-piperazinediones gave, after reduction of the nitro group and spontaneous cyclization, N-2-indolylcarbonylamino acid derivatives. A similar alcoholysis/reduction sequence applied to dehydrodipeptides bearing a 3(4)-nitroaryl substituent gave N-3(4)-aminophenyi-alpha-ketopropionylamino acid derivatives. Coupling of the free amino group with Boc-protected amino acids gave tripeptide mimetics with a 6-aminoindole-2-carboxylic or a 3(4)-aminophenyl-alpha-ketopropionic acid as the second residue. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6711 / 6714
页数：4
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