215303-72-3

Basic information

• Product Name: 4-[4-(4-Fluorophenyl)-1-(3-phenylpropyl)-5-(4-pyridinyl)-1H-imidazol-2-yl]-3-butyn-1-ol
• Synonyms: 4-[4-(4-Fluorophenyl)-1-(3-phenylpropyl)-5-(4-pyridinyl)-1H-imidazol-2-yl]-3-butyn-1-ol;RWJ 67657;4-(4-Fluorophenyl)-2-(4-hydroxy-1-butynyl)-1-(3-phenylpropyl)-5-(4-Pyridyl)iMidazole;JNJ 3026582
• CAS NO: 215303-72-3
• Molecular Formula: C₂₇H₂₄FN₃O
• Molecular Weight: 425
• Mol File: 215303-72-3.mol

Chemical Properties

• Melting Point: 124℃
• Boiling Point: 611.8°Cat760mmHg
• Flash Point: 323.8°C
• Appearance: /
• Density: 1.14g/cm³
• Vapor Pressure: 8.01E-16mmHg at 25°C
• Refractive Index: 1.599
• Storage Temp.: Store at RT
• Solubility: ≤10mg/ml in ethanol;5mg/ml in DMSO;2mg/ml in dimethyl formamide
• PKA: 14.37±0.10(Predicted)
• CAS DataBase Reference: 4-[4-(4-Fluorophenyl)-1-(3-phenylpropyl)-5-(4-pyridinyl)-1H-imidazol-2-yl]-3-butyn-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[4-(4-Fluorophenyl)-1-(3-phenylpropyl)-5-(4-pyridinyl)-1H-imidazol-2-yl]-3-butyn-1-ol(215303-72-3)
• EPA Substance Registry System: 4-[4-(4-Fluorophenyl)-1-(3-phenylpropyl)-5-(4-pyridinyl)-1H-imidazol-2-yl]-3-butyn-1-ol(215303-72-3)

Safety Data

• Hazardous Substances Data: 215303-72-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-[4-(4-Fluorophenyl)-1-(3-phenylpropyl)-5-(4-pyridinyl)-1H-imidazol-2-yl]-3-butyn-1-ol is used as a p38 mitogen-activated protein-kinase (p38MAPK) inhibitor for its potential role in intervening in the deranged immune response in sepsis and other inflammatory diseases. The compound has been shown to inhibit chemokine production and E-selectin expression in activated endothelial cells, making it a promising candidate for the development of new therapeutic strategies to combat these conditions.
Used in Research and Development:
In the field of research and development, 4-[4-(4-Fluorophenyl)-1-(3-phenylpropyl)-5-(4-pyridinyl)-1H-imidazol-2-yl]-3-butyn-1-ol can be utilized as a chemical probe to study the underlying mechanisms of various biological processes. Its unique structure allows for the investigation of protein-protein interactions, enzyme inhibition, and other cellular signaling pathways, contributing to a better understanding of disease pathology and the development of targeted therapies.
Used in Chemical Synthesis:
The compound can also be employed as a key intermediate in the synthesis of more complex molecules with potential applications in various industries, such as pharmaceuticals, agrochemicals, and materials science. Its versatile structure enables the development of novel compounds with improved properties, such as enhanced stability, selectivity, or bioavailability.

Biological Activity

rwj 67657 is an orally active inhibitor of the map kinases p38α and p38β.tumor necrosis factor-alpha (tnf-alpha), a cytokine secreted by activated monocytes/macrophages and t lymphocytes, is implicated in several disease states, such as inflammatory bowel disease, rheumatoid arthritis, septic shock, as well as osteoporosis. the monocyte/macrophage production of tnf-alpha is dependent on the mitogen-activated protein kinase p38.

in vitro

rwj 67657 could inhibit the release of tnf-alpha by lipopolysaccharide-treated human peripheral blood mononuclear cells, as well as the release of tnf-alpha from peripheral blood mononuclear cells treated with the superantigen staphylococcal enterotoxin b. rwj 67657 was about 10-fold more potent than the literature standard p38 kinase inhibitor sb 203580 in all tested p38 dependent in-vitro systems tested. moreover, rwj 67657 was able to inhibit the enzymatic activity of recombinant p38alpha and beta, but not gamma or delta, and showed no significant activity against various other enzymes. in contrast, sb 203580 could significantly inhibit the tyrosine kinases p56 lck and c-src. in addition, rwj 67657 did not inhibit t cell production of interleukin-2 or interferon-gamma and did not inhibit t cell proliferation in response to mitogens [1].

in vivo

animal study found that rwj 67657 could inhibit tnf-alpha production in lipopolysaccharide-injected mice (87% inhibition at 50 mg/kg) and in rats (91% inhibition at 25 mg/kg) after oral administration [1].

IC 50

1 and 11 μm for p38α and p38β, respectively

references

[1] wadsworth, s. a.,cavender, d.e.,beers, s.a., et al. rwj 67657, a potent, orally active inhibitor of p38 mitogen-activated protein kinase. journal of pharmacology and experimental therapeutics 291(2), 680-687 (1999).

InChI:InChI=1/C27H24FN3O/c28-24-13-11-22(12-14-24)26-27(23-15-17-29-18-16-23)31(25(30-26)10-4-5-20-32)19-6-9-21-7-2-1-3-8-21/h1-3,7-8,11-18,32H,5-6,9,19-20H2

Upstream product

• 927-74-2 3-Butyn-1-ol 

Relevant articles and documents

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