title: Synthesis of pyrazinone ring-containing opioid mimetics and examination of their opioid receptor-binding activity.
abstract: Cyclization of dipeptidyl chloromethyl ketones gave 6-(4-aminobutyl)-3-carboxyethyl-5-methyl-2(1H)-pyrazinone, 3-(4-aminobutyl)-6-carboxyethyl-5-methyl-2(1H)-pyrazinone, and 3,6-bis(4-aminobutyl)-5-methyl-2(1H)-pyrazinone, which were inserted into the enkephalin sequence to give opioid mimetics. Thus, it was confirmed that a pyrazinone ring can be easily inserted into a peptide sequence in order to evaluate structural components required for biologically active peptides.
authors.affiliation: Faculty of Pharmaceutical Sciences, Kobe Gakuin University, Japan. okada@pharm.kobegakuin.ac.jp
authors.forename: Y
authors.initials: Y
authors.lastname: Okada
authors.forename: A
authors.initials: A
authors.lastname: Fukumizu
authors.forename: M
authors.initials: M
authors.lastname: Takahashi
authors.forename: T
authors.initials: T
authors.lastname: Yokoi
authors.forename: Y
authors.initials: Y
authors.lastname: Tsuda
authors.forename: S D
authors.initials: SD
authors.lastname: Bryant
authors.forename: L H
authors.initials: LH
authors.lastname: Lazarus
mesh_terms: D002851:Chromatography, High Pressure Liquid; D003500:Cyclization; D018847:Opioid Peptides / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology*; D011719:Pyrazines / Q000138:chemical synthesis* / Q000494:pharmacology; D011957:Receptors, Opioid / Q000378:metabolism*; D017450:Receptors, Opioid, mu / Q000187:drug effects; D016339:Spectrometry, Mass, Fast Atom Bombardment
chemical_list: C121863:3,6-bis(4-aminobutyl)-5-methyl-2(1H)-pyrazinone; C121862:3-(4-aminobutyl)-6-carboxyethyl-5-methyl-2(1H)-pyrazinone; C121861:6-(4-aminobutyl)-3-carboxyethyl-5-methyl-2(1H)-pyrazinone; D018847:Opioid Peptides; D011719:Pyrazines; D011957:Receptors, Opioid; D017450:Receptors, Opioid, mu