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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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J K Yano et al.
The Journal of biological chemistry, 275(40), 31086-31092 (2000-06-22)
The structure of the first P450 identified in Archaea, CYP119 from Sulfolobus solfataricus, has been solved in two different crystal forms that differ by the ligand (imidazole or 4-phenylimidazole) coordinated to the heme iron. A comparison of the two structures
T Kimura et al.
Journal of medicinal chemistry, 36(11), 1641-1653 (1993-05-28)
In our continuing search to find systemically bioavailable ACAT (acyl-CoA:cholesterol O-acyltransferase) inhibitors with more potent antiatherosclerotic effect than N-[2-(dimethylamino)-6-[3-(5-methyl-4-phenyl-1H-imidazol-1-yl)propoxy] phenyl]-N'-pentylurea (3), a series of phenylureas linked to 4-phenylimidazole were synthesized and evaluated for in vitro inhibitory activity toward both aortic
Winny W Ho et al.
Biochemistry, 47(7), 2071-2079 (2008-01-17)
The crystal structure of a cytochrome P450 from the thermoacidophile Picrophilus torridus, CYP231A2 (PTO1399), has been solved. This structure reveals a wide open substrate access channel. To better understand ligand-induced structural transitions in CYP231A2, protein-ligand interactions were investigated using 4-phenylimidazole.
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
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
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