4-isothiocyanato-2-(trifluoroMethyl)benzonitrile Chemische Eigenschaften,Einsatz,Produktion Methoden
Verwenden
4-isothiocyanato-2-(trifluoroMethyl)benzonitrile is a reagent used to synthesize thioimidazolinone compounds and is a potential anti-prostate cancer drug. It is also used as an intermediate of enzalutamide.
Hazard
4-Isothiocyanato-2-(trifluoromethyl)benzonitrile is harmful when taken orally or in contact with the skin. It is irritating to the eyes and skin, and may cause allergic skin reactions; inhalation may cause respiratory irritation, allergic reactions, asthma symptoms or breathing difficulties.
Pharmazeutische Anwendungen
4-isothiocyanato-2-(trifluoroMethyl)benzonitrile participates in the synthesis of a PROTAC degraders of androgen receptor, which lead to a new therapy for AR+, castration-resistant prostate cancer
[1].
Synthese
4-Amino-2-trifluoromethylbenzonitrile, (2.23 g, 12 mmol) was added portionwise over15 minutes into the well-stirred heterogeneous mixture of thiophosgene (1 ml, 13 mmol) in water (22 ml) at room temperature. Stirring was continued for an additional 1 h. The reaction medium was extracted with chloroform (3 x 15 ml). The combined organic phase was dried over MgSO4 and evaporated to dryness under reduced pressure to yield desired product, 4-isothiocyanato-2-trifluoromethylbenzonitrile, (Ia), as brownish solid and was used as such for the next step (2.72 g, 11.9 mmol, 99%).
Einzelnachweise
[1] Han, X., Wang, C., Qin, C., Xiang, W., Fernandez-Salas, E., Yang, C.-Y., Wang, M., Zhao, L., Xu, T., Chinnaswamy, K., Delproposto, J., Stuckey, J., & Wang, S. (2019). Discovery of ARD-69 as a Highly Potent Proteolysis Targeting Chimera (PROTAC) Degrader of Androgen Receptor (AR) for the Treatment of Prostate Cancer. Journal of Medicinal Chemistry, 62 2, 941–964.
https://doi.org/10.1021/acs.jmedchem.8b01631
4-isothiocyanato-2-(trifluoroMethyl)benzonitrile Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
