214826-45-6Relevant articles and documents
Amino acids and peptides. LII. Design and synthesis of opioid mimetics containing a pyrazinone ring and examination of their opioid receptor binding activity
Okada, Yoshio,Tsukatani, Masaki,Taguchi, Hiroaki,Yokoi, Toshio,Bryant, Sharon D.,Lazarus, Lawrence H.
, p. 1374 - 1382 (2007/10/03)
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.