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New fMLF‐OMe Analogues Containing Constrained Mimics of Phenylalanine Residue
Author(s) -
Torrini Ines,
Mastropietro Gaia,
Zecchini Giampiero Pagani,
Paradisi Mario Paglialunga,
Lucente Gino,
Spisani Susanna
Publication year - 1998
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/(sici)1521-4184(199805)331:5<170::aid-ardp170>3.0.co;2-b
Subject(s) - residue (chemistry) , phenylalanine , chemistry , stereochemistry , chemical synthesis , combinatorial chemistry , biochemistry , in vitro , amino acid
In the context of a research program aimed at elucidating the HCO‐Met‐Leu‐Phe‐OMe (fMLF‐OMe) structural features which control interactions with the receptor in correspondence with the C ‐terminal residue, four different analogues of the native ligand have been synthesized and evaluated. Compounds 1‐3 possess the general formula HCO‐Met‐Leu‐Xaa‐OMe with Xaa = N ‐benzylglycine, N ‐benzylphenylalanine, and α,α‐dibenzylglycine, respectively. In the analogue 4 the constraint at the C ‐terminus has been obtained by incorporating a 2‐oxopiperazine ring, made up of two phenylalanine residues, to replace the native C ‐terminal Phe residue. The consequences of the chemical modifications on the activity of the new analogues are discussed.