Chemical and Pharmaceutical Bulletin p. 1374 - 1382 (1998)
Update date:2022-08-02
Topics:
Okada, Yoshio
Tsukatani, Masaki
Taguchi, Hiroaki
Yokoi, Toshio
Bryant, Sharon D.
Lazarus, Lawrence H.
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.
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