360556-35-0

Upstream product

• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 179678-69-4 N-p-methoxybenzyl-N-carboxymethyl-(S)-phenylalanine methyl ester 
• 179678-67-2 N-p-methoxybenzyl-N-(1-tert-butoxy-acet-2-yl)-(S)-phenylalanine methyl ester 
• 227623-99-6 2-(tert-butoxycarbonylmethyl-amino)-3-phenyl-propionic acid methyl ester 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 

Downstream Products

• 959367-60-3 Methanesulfonic acid (R)-[(2S,6S)-6-benzyl-1-(4-methoxy-benzyl)-4-methoxymethoxy-3,5-dioxo-piperazin-2-yl]-(4-methoxy-phenyl)-methyl ester 
• 959376-00-2 Methanesulfonic acid (R)-[(2S,6S)-6-benzyl-1-(4-methoxy-benzyl)-4-methoxymethoxy-3,5-dioxo-piperazin-2-yl]-(4-fluoro-phenyl)-methyl ester 
• 179679-01-7 (3S,5S)-3-Benzyl-5-[(R)-(4-fluoro-phenyl)-hydroxy-methyl]-4-(4-methoxy-benzyl)-1-methoxymethoxy-piperazine-2,6-dione 
• 179678-97-8 (3S,5S)-3-Benzyl-5-[(R)-hydroxy-(4-methoxy-phenyl)-methyl]-4-(4-methoxy-benzyl)-1-methoxymethoxy-piperazine-2,6-dione 
• 179678-98-9 (S)-3-Benzyl-4-(4-methoxy-benzyl)-1-methoxymethoxy-5-[1-(4-methoxy-phenyl)-meth-(Z)-ylidene]-piperazine-2,6-dione 
• 179679-02-8 (S)-3-Benzyl-5-[1-(4-fluoro-phenyl)-meth-(Z)-ylidene]-4-(4-methoxy-benzyl)-1-methoxymethoxy-piperazine-2,6-dione 
• 179678-94-5 (S)-3-Benzyl-4-(4-methoxy-benzyl)-1-methoxymethoxy-5-[2-methyl-prop-(Z)-ylidene]-piperazine-2,6-dione 
• 179678-73-0 1-methoxymethoxy-3S-benzyl-4-p-methoxybenzylpiperazine-2,6-dione 
• 179679-03-9 1-methoxymethoxy-3-benzyl-5-Z-p-fluorobenzylidene-3H-pyrazine-2,6-dione 
• 179678-99-0 5-Benzyl-1-methoxymethoxy-3-[1-(4-methoxy-phenyl)-meth-(Z)-ylidene]-3H-pyrazine-2,6-dione 
• 179678-72-9 (S)-3-Benzyl-1-hydroxy-4-(4-methoxy-benzyl)-piperazine-2,6-dione 
• 179678-96-7 5-Benzyl-1-methoxymethoxy-3-[2-methyl-prop-(Z)-ylidene]-3H-pyrazine-2,6-dione 
• 179679-04-0 5-Benzyl-3-[1-(4-fluoro-phenyl)-meth-(Z)-ylidene]-1-hydroxy-3H-pyrazine-2,6-dione 
• 360556-36-1 (S)-2-[Hydroxycarbamoylmethyl-(4-methoxy-benzyl)-amino]-3-phenyl-propionic acid methyl ester 

Relevant academic research and scientific papers

Synthesis of natural flutimide and analogous fully substituted pyrazine-2,6-diones, endonuclease inhibitors of influenza virus

Flutimide, a fully substituted 1-hydroxy-3H-pyrazine-2,6-dione, is a fungal metabolite isolated from a new species of Delitschia cofertaspora. It has been shown to selectively inhibit cap-dependent endonuclease activity of influenza virus A. The inhibition of this activity is a target for the potential development of a therapeutic agent to treat influenza infections. A convergent total synthesis of flutimide starting from L-leucine has been described. The synthetic methodology has been extended to include the synthesis of specifically designed aromatic analogues of flutimide, some of which exhibited greater than 7-fold improvement in activity. The most potent compounds were those with p-fluorobenzylidene or p-methoxybenzylidene substitutions at C-5 of 3H-pyrazine-2,6-dione and showed IC50 values of 0.9 and 0.8 μM, respectively. The details of the rationale for the synthetic design, syntheses, and biological activities of these analogues are described.