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1206880-66-1

1206880-66-1 Structure

1206880-66-1 Structure
IdentificationBack Directory
[Name]

AM-679
[CAS]

1206880-66-1
[Synonyms]

AM-679
AM-679;AM 679
(2-iodophenyl)(1-pentyl-1H-indol-3-yl)Me-thanon
(S)-3-(5-((1-acetylindolin-2-yl)methoxy)-3-(tert-Butylthio)-1-(4-(5-methoxypyrimidin-2-yl)benzyl)-1H-indol-2-yl)-2,2-dimethylpropanoic acid
3-{5-((S)-N-acetyl-2,3-dihydro-1H-indol-2-ylmethoxy)-3-tert-butylsulfanyl-1-[4-(5-methoxy-pyrimidin-2-yl)-benzyl]-1H-indol-2-yl}-2,2-dimethyl-propionic acid
1H-Indole-2-propanoic acid, 5-[[(2S)-1-acetyl-2,3-dihydro-1H-indol-2-yl]methoxy]-3-[(1,1-dimethylethyl)thio]-1-[[4-(5-methoxy-2-pyrimidinyl)phenyl]methyl]-α,α-dimethyl-
5-[[(2S)-1-Acetyl-2,3-dihydro-1H-indol-2-yl]methoxy]-3-[(1,1-dimethylethyl)thio]-1-[[4-(5-methoxy-2-pyrimidinyl)phenyl]methyl]-alpha,alpha-dimethyl-1H-indole-2-propanoic acid
[Molecular Formula]

C40H44N4O5S
[MDL Number]

MFCD20527236
[MOL File]

1206880-66-1.mol
[Molecular Weight]

692.87
Chemical PropertiesBack Directory
[Boiling point ]

837.1±65.0 °C(Predicted)
[density ]

1.23±0.1 g/cm3(Predicted)
[solubility ]

Soluble in DMSO
[form ]

crystalline solid
[pka]

4.69±0.10(Predicted)
Hazard InformationBack Directory
[Biological Activity]

am679 is a topically applied and potent 5-lipoxygenase-activating protein (flap) inhibitor with an ic50 value of 2.2 nm [1] [2].flap and 5-lipoxygenase (5-lo) together convert membrane-derived arachidonic acid to the pro-inflammatory mediator leukotriene epoxide lta4. lta4 is hence rapidly converted into either ltb4 by lta4 hydrolase or ltc4 by ltc4 synthase [2].incubation with am679 for an extended time period (5 h) increased the potency of human blood against ltb4 production with an ic50 value of 53 nm. this time-dependent increase also happened with an ic50 value of 9 nm in rat blood incubated with am679 for 4 h [2].cysteinyl leukotrienes (cyslts) are known as promoters of inflammation and allergy. mouse eye infected by rsv began to show increased ocular cyslts 4 days after infection. am679 decreased the peak 6- to 8-day of ocular cyslts by more than 90%. by day 10, concentrations of cyslt for both am679-treated mouse eyes and control had almost returned to the baseline. a strong correlation between rsv and il-4 mrna had been found for human allergic conjunctivitis. 6 days after rsv infection, il-4 mrna concentrations were significantly elevated in rsv-infected mouse eyes. around 14 days, il-4 mrna concentrations were hence gradually decreased to near baseline. am679 could inhibit more than 80% of the il-4 increase resulted from rsv infection [1].
[target]

FLAP
[References]

[1]. alla musiyenko, lucia correa, nicholas stock, et al. a novel 5-lipoxygenase-activating protein inhibitor, am679, reduces inflammation in the respiratory syncytial virus-infected mouse eye. clinical and vaccine immunology, 2009, 16(11):1654-1659.
[2]. nicholas stock, christopher baccei, gretchen bain, et al. 5-lipoxygenase-activating protein inhibitors. part 2: 3-{5-((s)-1-acetyl-2,3-dihydro-1h-indol-2-ylmethoxy)-3-tert-butylsulfanyl-1-[4-(5-methoxy-pyrimidin-2-yl)-benzyl]-1h-indol-2-yl}-2,2-dimethyl-propionic acid (am679)—a potent flap inhibitor. bioorganic & medicinal chemistry letters, 2010, 20:213-217.
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