234450-08-9Relevant academic research and scientific papers
Amino acids and peptides. LVI. Synthesis of pyrazinone ring-containing opioid mimetics and examination of their opioid receptor binding activity
Okada, Yoshio,Fukumizu, Atsuko,Takahashi, Motohiro,Yamazaki, Junpei,Yokoi, Toshio,Tsuda, Yuko,Bryant, Sharon D.,Lazarus, Lawrence H.
, p. 14391 - 14406 (1999)
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)-5-methyl-2(1H)- pyrazinone (15). Using above pyrazinone derivatives, three opioid mimetics were prepared (III-V). Derivatives containing 3 and 6 demonstrated weak μ and δ-opioid receptor affinities ranging from 1.6 mM to 4.1 mM while the opioid mimetic containing derivative 15 displayed higher μ-opioid receptor binding affinity (K(i)μ = 61 nM) and selectivity (K(i)μ/K(i) δ = 31).
Synthesis of pyrazinone ring-containing opioid mimetics and examination of their opioid receptor-binding activity
Okada, Yoshio,Fukumizu, Atsuko,Takahashi, Motohiro,Yokoi, Toshio,Tsuda, Yuko,Bryant, Sharon D.,Lazarus, Lawrence H.
, p. 1193 - 1195 (2007/10/03)
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.
