6240-10-4Relevant articles and documents
γ-aminoadamantanecarboxylic acids through direct C-H bond amidations
Wanka, Lukas,Cabrelle, Chiara,Vanejews, Maksims,Schreiner, Peter R.
, p. 1474 - 1490 (2008/09/19)
Utilizing bromine-free, direct C-H bond amidations we have synthesized a large variety of adamantane amides. Depending on the precursors used these amides directly yield pharmaceutically active aminoadamantanes or γ-aminoadamantanecarboxylic acids after hydrolytic cleavage. These rigid analogues of γ-aminobutyric acid (GABA) were protected at the C- and N-termini and we synthesized a number of peptides incorporating γ-aminoadamantanecarboxylic acids in solution as well as via solid phase peptide synthesis. These peptides are promising scaffolds for applications in medicinal chemistry as well as in organocatalysis. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
N-Adamantane-substituted tetrapeptide amides
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, (2008/06/13)
N-Adamantane-substituted tetrapeptide amides and the pharmacologically acceptable salts thereof are disclosed herein. These compounds are analogs of enkephalin wherein the methionine or leucine of position 5 has been substituted by an adamantyl amide and the glycine of position 2 has been substituted by various amino acid residues. Optionally the tyrosine of position 1 and the phenylalanine of position 4 may be substituted by various amino acid residues. These compounds exhibit agonist activity at opiate receptor sites and are useful as analgesics.
