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144754

Sigma-Aldrich

4-Phenylimidazol

97%

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About This Item

Empirische Formel (Hill-System):
C9H8N2
CAS-Nummer:
670-95-1
Molekulargewicht:
144.17
Beilstein:
2969
EG-Nummer:
211-580-1
MDL-Nummer:
MFCD00005197
UNSPSC-Code:
12352005
PubChem Substanz-ID:
24848681
NACRES:
NA.22

Assay

97%

mp (Schmelzpunkt)

128-131 °C (lit.)

Löslichkeit

acetone: soluble 25 mg/mL, clear, colorless to yellow (typical)

SMILES String

c1ccc(cc1)-c2c[nH]cn2

InChI

1S/C9H8N2/c1-2-4-8(5-3-1)9-6-10-7-11-9/h1-7H,(H,10,11)

InChIKey

XHLKOHSAWQPOFO-UHFFFAOYSA-N

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Anwendung

4-Phenylimidazole was used to investigate the protein-ligand interactions in cytochrome P450 from the thermoacidophile Picrophilus torridus. It was used as heme ligand during the crystallization of recombinant human indoleamine 2,3-dioxygenase. It was used in the synthesis of complexes of copper and cobalt.

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

Gefahreneinstufungen

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves

Analysenzertifikate (COA)

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M Spatzenegger et al.
Molecular pharmacology, 59(3), 475-484 (2001-02-17)
The molecular basis for reversible inhibition of rabbit CYP2B4 and CYP2B5 and rat CYP2B1 by phenylimidazoles was assessed with active-site mutants and new three-dimensional models based on the crystal structure of CYP2C5. 4-Phenylimidazole was 17- to 32-fold more potent toward
Danni L Harris et al.
Proteins, 55(4), 895-914 (2004-05-18)
The molecular origins of temperature-dependent ligand-binding affinities and ligand-induced heme spin state conversion have been investigated using free energy analysis and DFT calculations for substrates and inhibitors of cytochrome P450 2B4 (CYP2B4), employing models of CYP2B4 based on CYP2C5(3LVdH)/CYP2C9 crystal
Y K Li et al.
Biochimica et biophysica acta, 999(3), 227-232 (1989-12-21)
Over 25 nitrogen-containing heterocycles were tested as inhibitors of sweet almond beta-glucosidase (EC 3.2.1.21). Among the most potent of these are some imidazole derivatives. The pH dependence indicates that the unprotonated inhibitor binds most tightly to the catalytically active species
Spectral and metabolic properties of liver microsomes from imidazole-pretreated rabbits.
K K Hajek et al.
Biochemical and biophysical research communications, 108(2), 664-672 (1982-09-30)
Y K Li et al.
Journal of biochemistry, 123(3), 416-422 (1998-05-30)
Series of 4-arylimidazoles, omega-N-acylhistamines and 4-(omega-phenylalkyl)imidazoles were synthesized in order to probe the active site topology of sweet almond beta-glucosidase. These imidazole derivatives were shown to be very powerful competitive inhibitors. Among the 20 tested compounds, omega-N-benzoylhistamine and 4-(3'-phenylpropyl)imidazole are
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