121071-92-9

Basic information

• Product Name: 6-(1H-indol-3-ylmethyl)-5-methoxy-3-(2-methylpropyl)pyrazin-2(1H)-one 4-oxide
• Synonyms: 2(1H)-Pyrazinone, 6-(1H-indol-3-ylmethyl)-5-methoxy-3-(2-methylpropyl)-, 4-oxide
• CAS NO: 121071-92-9
• Molecular Formula: C₁₈H₂₁N₃O₃
• Molecular Weight: 327.3776
• Mol File: 121071-92-9.mol
• Article Data: 6

Chemical Properties

• Density: 1.25g/cm³
• Refractive Index: 1.63
• CAS DataBase Reference: 6-(1H-indol-3-ylmethyl)-5-methoxy-3-(2-methylpropyl)pyrazin-2(1H)-one 4-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 6-(1H-indol-3-ylmethyl)-5-methoxy-3-(2-methylpropyl)pyrazin-2(1H)-one 4-oxide(121071-92-9)
• EPA Substance Registry System: 6-(1H-indol-3-ylmethyl)-5-methoxy-3-(2-methylpropyl)pyrazin-2(1H)-one 4-oxide(121071-92-9)

Safety Data

• Hazardous Substances Data: 121071-92-9(Hazardous Substances Data)

Upstream product

• 4299-70-1 L-tryptophan methyl ester 
• 7303-49-3 DL-tryptophan methyl ester 
• 131827-99-1 (S)-N-(2-hydroxyimino-4-methylvaleryl)tryptophan methyl ester 
• 131828-02-9 (S)-N-(2-hydroxyimino-4-methylvaleryl)tryptophan 
• 138039-95-9 2-{2-[(E)-Hydroxyimino]-4-methyl-pentanoylamino}-3-(1H-indol-3-yl)-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester 
• 131827-28-6 2-(tert-butoxycarbonyloxy)-5-hydroxy-6-(1H-indol-3-ylmethyl)-3-(2-methylpropyl)pyrazine 4-oxide 
• 131827-99-1 N-(2-hydroxyimino-4-methylvaleryl)tryptophan methyl ester 
• 131828-02-9 N-(2-hydroxyimino-4-methylvaleryl)tryptophan 
• 131827-27-5 5-hydroxy-6-(1H-indol-3-ylmethyl)-3-(2-methylpropyl)pyrazin-2(1H)-one 4-oxide 
• 76617-78-2 2-(hydroxyimino)-4-methylpentanoic acid 
• 298696-11-4 N-[2-(2-cyanoethoxyimino)isohexanoyl]-N-(2-cyanoethyl)-L-tryptophan methyl ester 
• 168766-86-7 N-(2-cyanoethyl)-N-(2-hydroxyiminoisohexanoyl)-L-tryptophan benzyl ester 
• 168766-50-5 1-(2-cyanoethyl)-3-isobutyl-5-hydroxy-6-(indol-3-yl)-methyl-1,2-dihydropyrazin-2-one 4-oxide 
• 168766-51-6 1-(2-cyanoethyl)-3-isobutyl-5-methoxy-6-(indol-3-yl)-methyl-1,2-dihydropyrazin-2-one 4-oxide 

Relevant articles and documents

Progress in the synthesis of OPC-15161: Easy access to dioxygenated pyrazine N-oxide structure

An improved synthetic route to OPC-15161 (1), a novel inhibitor of superoxide anion generation, is described. Choice of the protecting group is the key to the second-generation synthesis. Usefulness of the 2-cyanoethyl (CE)-protecting group in our process research is emphasized in comparison with that of other protecting groups. This process can be carried out in four steps with 40% overall yield from tryptophan methyl ester, which also opens a general route for the preparation of the related 5-alkoxypyrazin-2(1H)-one 4-oxides.

Synthesis of 2,5-Dioxygenated Pyrazine 4-Oxides: Total Synthesis of a New Inhibitor of Superoxide Anion Generation, OPC-15161

The total synthesis of OPC-15161 1, a new inhibitor of superoxide anion generation, is described in full.Three approaches, routes A-C, have been investigated focusing on the pivotal structure 2,5-dioxygenated pyrazine 4-oxide.Among them, route A led to the total synthesis of 1.That is, the key precursor, 5-hydroxypyrazin-2(1H)-one 4-oxide 7 has been prepared from tryptophan methyl ester 2 in three steps, and direct methylation of the 5-hydroxy group of 7 or three-step methylation via the 2-O-Boc derivative 10 afforded 1 in 9.9-10.6percent overall yields.

TOTAL SYNTHESIS OF A NEW INHIBITOR OF SUPEROXIDE ANION GENERATION, OPC-15161

The first total synthesis of a new inhibitor of superoxide anion generation, OPC-15161, was achieved from tryptophan methyl ester in 4-6 steps in 9.9-10.6percent overall yields.