2-AMINO-3-OXOHEXAHYDROINDOLIZINO[8,7-B]INDOLE-5-CARBOXYLATE DERIVATIVES AS NEW SCAFFOLDS FOR MIMICKING BETA-TURN SECONDARY STRUCTURES - MOLECULAR-DYNAMICS AND STEREOSELECTIVE SYNTHESIS

被引：38

作者：

DELAFIGUERA, N ^{[1
]}

ALKORTA, I ^{[1
]}

GARCIALOPEZ, MT ^{[1
]}

HERRANZ, R ^{[1
]}

GONZALEZMUNIZ, R ^{[1
]}

机构：

[1] CSIC,INST QUIM MED,E-28006 MADRID,SPAIN

来源：

TETRAHEDRON | 1995年 / 51卷 / 28期

关键词：

D O I：

10.1016/0040-4020(95)00402-T

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly constrained 2-amino-3-oxohexahydroindolizino[8-7-b]indole-5-carboxylate derivatives of general formula 1 have been developed as novel beta-turn mimetics. Molecular dynamics studies on model structures 2a and 2b have revealed that both indolizinoindole derivatives are able to adopt conformations close to those of ideal type II' beta-turn. The asymmetric synthesis of this heterocyclic system was accomplished from 1,3-di- and 1,2,3-trisubstituted tetrahydro-beta-carbolines, which were prepared in stereoselective or stereospecific way by application of the Pictet-Spengler reaction.

引用

页码：7841 / 7856

页数：16