4-(1H-Imidazol-1-yl)aniline

Chemical Properties

White powder

Uses

LANA-IN-1 (compound 8) is an N-acetyl-derived LANA inhibitor with antiviral activity against herpesvirus. In fluorescence assays using the LANA probe LBS2, 1 mM LANA-IN-1 shows an inhibition rate of 32%. LANA-IN-1 may inhibit the interaction between LANA and the viral genome[1].

Synthesis

GENERAL METHODS: In a catalyzed reaction, Catalyst C1 (12 mg, 0.01 mmol), imidazole (1.0 mmol), 4-bromoaniline (1.0 mmol), NaOH (80 mg, 2.0 mmol), and dimethyl sulfoxide (DMSO, 5 mL) were added to a sealed tube. The reaction mixture was stirred at 100 °C for 4 h and subsequently cooled to room temperature. After the reaction was completed, 5 mL of water was added and the mixture was extracted with ethyl acetate (5 mL x 3). The organic layers were combined, dried with anhydrous Na2SO4 and concentrated under reduced pressure to remove the solvent. Finally, the target product 4-(imidazol-1-yl)aniline was purified by silica gel column chromatography.

References

[1] Kirsch P, et al. Fragment-Based Discovery of a Qualified Hit Targeting the Latency-Associated Nuclear Antigen of the Oncogenic Kaposi's Sarcoma-Associated Herpesvirus/Human Herpesvirus 8. J Med Chem. 2019 Apr 25;62(8):3924-3939. DOI:10.1021/acs.jmedchem.8b01827