234450-09-0

Basic information

• Product Name: 6-[4-(N^α-Boc-Tyr)-aminobutyl]-3-[2-(Phe-OBu^t)-carbonylethyl]-5-methyl-2(1H)-pyrazinone
• Synonyms: 6-[4-(N^α-Boc-Tyr)-aminobutyl]-3-[2-(Phe-OBu^t)-carbonylethyl]-5-methyl-2(1H)-pyrazinone
• CAS NO: 234450-09-0
• Molecular Weight: 719.879
• Mol File: 234450-09-0.mol

Chemical Properties

• CAS DataBase Reference: 6-[4-(N^α-Boc-Tyr)-aminobutyl]-3-[2-(Phe-OBu^t)-carbonylethyl]-5-methyl-2(1H)-pyrazinone(CAS DataBase Reference)
• NIST Chemistry Reference: 6-[4-(N^α-Boc-Tyr)-aminobutyl]-3-[2-(Phe-OBu^t)-carbonylethyl]-5-methyl-2(1H)-pyrazinone(234450-09-0)
• EPA Substance Registry System: 6-[4-(N^α-Boc-Tyr)-aminobutyl]-3-[2-(Phe-OBu^t)-carbonylethyl]-5-methyl-2(1H)-pyrazinone(234450-09-0)

Safety Data

• Hazardous Substances Data: 234450-09-0(Hazardous Substances Data)

Upstream product

• 3978-80-1 Boc-Tyr-OH 
• 16874-17-2 L-phenylalanine tert-butyl ester 
• 234450-07-8 6-[4-(9-fluorenylmethoxycarbonyl)-aminobutyl]-3-(2-carboxyethyl)-5-methyl-2(1H)-pyrazinone 
• 234450-08-9 6-[4-(9-fluorenylmethoxycarbonyl)-aminobutyl]-3-[2-(Phe-OBu^t)-carbonylethyl]-5-methyl-2(1H)-pyrazinone 

Relevant articles and documents

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

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.

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

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).