586379-66-0

Basic information

• Product Name: PH 797804
• Synonyms: PH 797804;3-Bromo-4-[(2,4-difluorobenzyl)oxy]-1-[5-[(methylamino)carbonyl]-2-methylphenyl]-6-methylpyridin-2(1H)-one;3-(3-Bromo-4-((2,4-difluorobenzyl)oxy)-6-methyl-2-oxopyridin-1(2H)-yl)-N,4-dimethylbenzamide;3-(4-(2,4-difluorobenzyloxy)-3-bromo-6-methyl-2-oxopyridin-1(2H)-yl)-N,4-dimethylbenzamide;PH-797804, >=98%
• CAS NO: 586379-66-0
• Molecular Formula: C₂₂H₁₉BrF₂N₂O₃
• Molecular Weight: 477.2986664
• Product Categories: Inhibitors;MAPK
• Mol File: 586379-66-0.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 593.206 °C at 760 mmHg
• Flash Point: 312.56 °C
• Appearance: /
• Density: 1.51
• Storage Temp.: 20-25°C
• Solubility: ≥23.85 mg/mL in DMSO; insoluble in H2O; insoluble in EtOH
• CAS DataBase Reference: PH 797804(CAS DataBase Reference)
• NIST Chemistry Reference: PH 797804(586379-66-0)
• EPA Substance Registry System: PH 797804(586379-66-0)

Safety Data

• Hazardous Substances Data: 586379-66-0(Hazardous Substances Data)

Usage

Description

PH 797804 is a novel N-phenylpyridinone inhibitor of p38 mitogen-activated protein (MAP) kinase, derived from a racemic mixture as the more potent atropisomer. It is a member of the class of benzamides obtained by formal condensation of the carboxy group of 3-3-bromo-4-[(2,4-difluorobenzyl)oxy]-6-methyl-2-oxopyridin-1-yl-4-methylbenzoic acid with the amino group of methylamine. PH 797804 is known for its anti-inflammatory properties and potential applications in various industries.

Uses

Used in Pharmaceutical Industry:
PH 797804 is used as an inhibitor for p38 mitogen-activated protein (MAP) kinase for its anti-inflammatory properties. It is particularly useful in the development of treatments for inflammatory diseases and conditions, as it can help modulate the immune response and reduce inflammation.
Used in Research and Development:
PH 797804 is used as a research tool for studying the role of p38 MAP kinase in various cellular processes and disease pathways. Its potent inhibitory activity allows researchers to investigate the specific functions and interactions of this kinase in cellular signaling and inflammation.
Used in Drug Discovery:
PH 797804 serves as a starting point for the development of new drugs targeting p38 MAP kinase. Its structure and activity can be further optimized to improve potency, selectivity, and pharmacokinetic properties, leading to the discovery of more effective therapeutic agents for treating inflammatory diseases and other related conditions.

Biological Activity

ph-797804 is a novel, potent, atp-competitive and reversible inhibitor of human p38 map kinase. it specifically inhibits p38α with ic50 value of 26 nm and k(i) value of 5.8 nm.ph-797804 inhibits lps induced tnf-α and il-1β production in monocytes with a concentration-dependently manner. ph-797804 blocks rankl and m-csf induced osteoclast formation in primary rat bone marrow cells.orally administered ph-797804 suppresses tnf-α level in a dose-dependent manner in lps induced lewis rats and also in cynomolgus monkeys. additionally, ph-797804 has been shown to inhibit chronic inflammation in arthritis models induced by mouse collagen-induced or rat streptococcal cell wall (scw) extract.

Biochem/physiol Actions

PH-797804 is an orally active, potent and readily reversible ATP competitive inhibitor of the alpha isoform of human p38 MAP kinase. PH-797804 blocks inflammation-induced production of cytokines and proinflammatory mediators.

references

[1] hope hr1, anderson gd, burnette bl, compton rp, devraj rv, hirsch jl, keith rh, li x, mbalaviele g, messing dm, saabye mj,schindler jf, selness sr, stillwell li, webb eg, zhang j, monahan jb. anti-inflammatory properties of a novel n-phenyl pyridinone inhibitor of p38 mitogen-activated protein kinase: preclinical-to-clinical translation. j pharmacol exp ther. 2009 dec;331(3):882-95.

Upstream product

• 74-89-5 methylamine 
• 18595-18-1 3-amino-4-methyl benzoic acid methyl ester 
• 586379-70-6 methyl 3-(4-(2,4-difluorobenzyloxy)-3-bromo-6-methyl-2-oxopyridin-1(2H)-yl)-4-methylbenzoate 
• 1033909-28-2 methyl 3-(3-bromo-4-hydroxy-6-methyl-2-oxopyridin-1(2H)-yl)-4-methylbenzoate 
• 586379-64-8 3-(5-bromo-4-((2,4-difluorobenzyl)oxy)-6-methyl-2-oxopyridin-1(2H)-yl)-4-methylbenzoic acid 
• 586379-61-5 methyl 3-(4-hydroxy-6-methyl-2-oxopyridin-1(2H)-yl)-4-methylbenzoate 
• 675-10-5 4-hydroxy-6-methyl-2-pyron 

Downstream Products

• 1358027-80-1 (-)-3-(4-(2,4-difluorobenzyloxy)-3-bromo-6-methyl-2-oxopyridin-1(2H)-yl)-N,4-dimethylbenzamide 

Relevant articles and documents

Discovery of PH-797804, a highly selective and potent inhibitor of p38 MAP kinase

The synthesis and SAR studies of a novel N-aryl pyridinone class of p38 kinase inhibitors are described. Systematic structural modifications to the HTS lead, 5, led to the identification of (-)-4a as a clinical candidate for the treatment of inflammatory diseases. Additionally, the chiral synthesis and properties of (-)-4a are described.