214826-65-0

Upstream product

• 2389-45-9 Boc-Lys(Z)-OH 
• 84890-96-0 C₂₄H₃₆N₂O₈ 
• 108524-68-1 2-((tert-butoxycarbonyl)amino)-4-phenylbutanoic acid 
• 214826-38-7 Boc-DL-homophenylalanine-CH₂Cl 
• 214826-50-3 Boc-Lys(Z)-DL-Hfe-CH₂Cl 

Downstream Products

• 214826-80-9 3-<4-(N^α-Boc-Tyr)-aminobutyl>-5-methyl-6-β-phenethyl-2(1H)-pyrazinone 

Relevant academic research and scientific papers

Design and synthesis of opioidmimetics containing 2′,6′-dimethyl-l-tyrosine and a pyrazinone-ring platform

Twelve 2′,6′-dimethyl-l-tyrosine (Dmt) analogues linked to a pyrazinone platform were synthesized as 3- or 6-[H-Dmt-NH(CH2)n],3- or 6-R-2(1H)-pyrazinone (n = 1-4). 3-[H-Dmt-NH-(CH2)4]-6-β-phenethyl-5-methyl-2(1H)-pyrazinone 11 bound to μ-opioid receptors with high affinity (Kiμ = 0.13 nM; Kiδ/Kiμ = 447) with μ-agonism (GPI IC50 = 15.9 nM) and weak δ-antagonism (MVD pA2 = 6.35). Key factors affecting opioid affinity and functional bioactivity are the length of the aminoalkyl chain linked to Dmt and the nature of the R residue. These data present a simplified method for the formation of pyrazinone opioidmimetics and new lead compounds.

Amino acids and peptides. LII. Design and synthesis of opioid mimetics containing a pyrazinone ring and examination of their opioid receptor binding activity

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.