A Constrained Diketopiperazine as a New Scaffold for the Synthesis of Peptidomimetics

As a new scaffold for peptidomimetic synthesis, a highly constrained bifunctional diketopiperazine, 4, has been prepared by smooth N‐alkylation with tert‐butyl bromoacetate. As a first application, we describe herein the synthesis of new peptidomimetics of the Arg‐Gly‐Asp (RGD) sequence. The product...

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Bibliographic Details
Published inEuropean journal of organic chemistry Vol. 1998; no. 5; pp. 853 - 859
Main Authors Pons, Jean-François, Fauchère, Jean-Luc, Lamaty, Frédéric, Molla, Annie, Lazaro, René
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag GmbH 01.05.1998
WILEY‐VCH Verlag GmbH
Wiley
Subjects
Chemistry
Chemistry, Organic
Diketopiperazine building block
N-Alkylation
Peptidomimetics
Physical Sciences
RGD analogues
Science & Technology
BINDING INTERACTION
DESIGN
IIB-IIIA RECEPTOR
PLATELET-AGGREGATION
ASP-PHE SEQUENCE
PROPOSAL
RGD analogues
N-alkylation
diketopiperazine building block
POTENT
RGDX MIMETICS
FIBRINOGEN RECEPTOR ANTAGONISTS
peptidomimetics
INHIBITORS
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Summary:As a new scaffold for peptidomimetic synthesis, a highly constrained bifunctional diketopiperazine, 4, has been prepared by smooth N‐alkylation with tert‐butyl bromoacetate. As a first application, we describe herein the synthesis of new peptidomimetics of the Arg‐Gly‐Asp (RGD) sequence. The product 30, which shows a selective platelet‐aggregation inhibiting activity, can be used as a lead for the preparation of more potent products.
Bibliography:istex:3A2E160FAC0FCBFDEB6DF13BC85728C7BBE4C6DB
ark:/67375/WNG-DV85MFPL-4
ArticleID:EJOC853
ISSN:1434-193X
1099-0690
DOI:10.1002/(SICI)1099-0690(199805)1998:5<853::AID-EJOC853>3.0.CO;2-F