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A Constrained Diketopiperazine as a New Scaffold for the Synthesis of Peptidomimetics
Author(s) -
Pons JeanFrançois,
Fauchère JeanLuc,
Lamaty Frédéric,
Molla Annie,
Lazaro René
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199805)1998:5<853::aid-ejoc853>3.0.co;2-f
Subject(s) - peptidomimetic , chemistry , scaffold , bifunctional , alkylation , combinatorial chemistry , sequence (biology) , stereochemistry , platelet aggregation , organic chemistry , biochemistry , peptide , catalysis , platelet , medicine , biomedical engineering , immunology , biology
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.