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Amino acids and peptides. LVI. Synthesis of pyrazinone ring-containing opioid mimetics and examination of their opioid receptor binding activity

✍ Scribed by Yoshio Okada; Atsuko Fukumizu; Motohiro Takahashi; Junpei Yamazaki; Toshio Yokoi; Yuko Tsuda; Sharon D Bryant; Lawrence H Lazarus

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 976 KB
Volume: 55
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(99)00908-4

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✦ Synopsis

Cyclization of dipeptidyl chloromethyl ketones gave 6-(4-aminobutyl)-3-carboxyethyl-5-methyl-2(1H)pyrazinone (3), 3-(4-aminobutyl)-6-carboxyethyl-5-methyl-2(1H)-pyrazinone (6), and 3,6-bis(4-aminobutyl)-5methyl-2(1H)-pyrazinone (15). Using above pyrazinone derivatives, three opioid mimetics were prepared (III-V). Derivatives containing 3 and 6 demonstrated weak I.t and 15-opioid receptor affinities ranging from 1.6 mM to 4.1 mM while the opioid mimetic containing derivative 15 displayed higher p.-opioid receptor binding affinity (K, I1 = 61 nM) and selectivity (K, ta/K~ 8 = 31).

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