Synthesis of pyrazinone ring-containing opioid mimetics and examination of their opioid receptor-binding activity

Chemical and Pharmaceutical Bulletin

Volumn 47, Issue 8, 1999, Pages 1193-1195

  Okada, Yoshio ^a   Fukumizu, Atsuko ^a   Takahashi, Motohiro ^a   Yokoi, Toshio ^a   Tsuda, Yuko ^a   Bryant, Sharon D ^b   Lazarus, Lawrence H ^b  

^a KOBE GAKUIN UNIVERSITY   (Japan)

^b NATIONAL INSTITUTE OF ENVIRONMENTAL HEALTH SCIENCES   (United States)

Author keywords

Enkephalin sequence; Opioid mimetic; Peptide mimetic; Pyrazinone ring; Receptor binding activity; selective

Indexed keywords

3 (4 AMINOBUTYL) 6 CARBOXYETHYL 5 METHYL 2(1H) PYRAZINONE; 3,6 BIS(4 AMINOBUTYL) 5 METHYL 2(1H) PYRAZINONE; 6 (4 AMINOBUTYL) 3 CARBOXYETHYL 5 METHYL 2(1H) PYRAZINONE; OPIATE AGONIST; UNCLASSIFIED DRUG;

ARTICLE; DRUG CONFORMATION; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION;

EID: 0032869694     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.47.1193     Document Type: Article

References (3)

1. The customary L-configuration for amino acid residues is omitted. Abbreviations used in this report for amino acids, peptides and the derivatives are those recommended by the IUPAC-IUB Commission on Biochemical Nomenclature: Biochemistry, 5, 2485-2489 (1966);
2. 6, 362-364 (1966);
3. 11, 1726-1732 (1972). The following additional abbreviations are used: TFA, trifluoroacetic acid; Z, benzyloxycarbonyl; Boc, tert-butyloxycarbonyl; OBu′, tert-butyl ester; Fmoc, 9-fluorenylmethyloxycarbonyl; OSu, N-hydroxysuccinimide ester; BOP, Benzotriazol-1-yl-oxy-tris(dimethylamino)phosphonium hexafluorophosphate; GPI, guinea pig ileum; MVD, mouse vas deferens.