Amino acids and peptides. LII. Design and synthesis of opioid mimetics containing a pyrazinone ring and examination of their opioid receptor binding activity

Article abstract of DOI:10.1248/cpb.46.1374

An amino group was introduced to the 3 or 6 position of a pyrazinone ring by cyclization of dipeptidyl chloromethyl ketones. Boc-Tyr-OH was coupled with the amino function, followed by removal of the Boc group to give pyrazinone ring-containing tyrosine derivatives. Of the various tyrosine derivatives prepared, 5-methyl-6-β-phenethyl-3-tyrosylaminobutyl-2(1H)- pyrazinone exhibited strong binding to the μ-opioid receptor with a K(i) value of 55.8 nM and to the δ-opioid receptor with a K(i) value of 2165 nM and with a K(i)μ/K(i)δ value of 0.026.

Full text of DOI:10.1248/cpb.46.1374

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