1194235-21-6

Basic information

• Product Name: N-(2-pyrazinecarbonyl)-L-phenylalanine-L-(2-naphthyl)-alanine
• Synonyms: N-(2-pyrazinecarbonyl)-L-phenylalanine-L-(2-naphthyl)-alanine
• CAS NO: 1194235-21-6
• Molecular Weight: 468.512
• Mol File: 1194235-21-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N-(2-pyrazinecarbonyl)-L-phenylalanine-L-(2-naphthyl)-alanine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-pyrazinecarbonyl)-L-phenylalanine-L-(2-naphthyl)-alanine(1194235-21-6)
• EPA Substance Registry System: N-(2-pyrazinecarbonyl)-L-phenylalanine-L-(2-naphthyl)-alanine(1194235-21-6)

Safety Data

• Hazardous Substances Data: 1194235-21-6(Hazardous Substances Data)

Upstream product

• 1194235-07-8 (S)-methyl 3-(naphthalen-2-yl)-2-((S)-3-phenyl-2-(pyrazine-2-carboxamido)-propanamido) propanoate 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 73058-37-4 N-(2-pyrazinylcarbonyl)-L-phenylalanine methyl ester 
• 98-97-5 2-pyrazylcarboxylic acid 

Downstream Products

• 1194235-34-1 (+)-pinanediol N-(2-pyrazinecarbonyl)-L-phenylalanine-L-(2-naphthyl)-alanine-L-leucineboronate 

Relevant articles and documents

Synthesis and biological activity of peptide proline-boronic acids as proteasome inhibitors

On the basis of the application of proline-boronic acid as pharmacophore in the kinase inhibitors and our previous research results, using proline-boronic acid as warhead, two series of peptide proline-boronic acids, dipeptide proline-boronic acids (I) and tripeptide proline-boronic acids (II), were designed and synthesized. All the synthesized compounds were first evaluated for their biological activity against MGC803 cell, and then, the best compound II-7 was selected to test its anti-tumor spectrum on six human tumor cell lines and proteasome inhibition against three subunits. The results indicated that series II have much better biological activities than series I. The compound II-7 exhibited not only excellent biological activities with IC50 values of nM level in both cell and proteasome models, but also much better subunit selectivity. Thus, proline-boronic acid as warhead is reasonable in the design of proteasome inhibitors.

Design, synthesis and biological evaluation of tripeptide boronic acid proteasome inhibitors

A series of tripeptide boronate proteasome inhibitors were designed and synthesized on the basis of our previously built tripeptide aldehyde 3D-QSAR models. All the synthesized compounds were evaluated for their proteasome-inhibitory activities in an isolated 20S rabbit proteasome, and selected compounds were evaluated for their antitumor activities in vitro against four human cancer cell lines. Biological results showed bulky and negative substituents at P2 position improved the proteasome-inhibitory potency obviously, which completely conformed to the theoretical models, while those at P3 position thoroughly deviated from the 3D-QSAR model. Most of the screened compounds showed less than 1 nM inhibitory potency and high selectivity against 20S proteasome, of which 7f is the most potent (IC50 = 0.079 nM) and twofold more active than bortezomib (IC50 = 0.161 nM). Cell viability indicated hydrophilic 4-hydroxyphenyl substituent at P2 or P3 position was not favorable to the cellular activities. Especially for the two hematologic cancer cell lines, HL-60 and U266, 7f inhibited them at the level of less than 10 nM and was more potent than the control bortezomib. It is being considered a promising new lead to be developed for the treatment of various cancers.