1019972-88-3

Basic information

• Product Name: (R)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-methyloxirane-2-carboxamide
• Synonyms: (R)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-methyloxirane-2-carboxamide
• CAS NO: 1019972-88-3
• Molecular Weight: 270.211
• Mol File: 1019972-88-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (R)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-methyloxirane-2-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-methyloxirane-2-carboxamide(1019972-88-3)
• EPA Substance Registry System: (R)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-methyloxirane-2-carboxamide(1019972-88-3)

Safety Data

• Hazardous Substances Data: 1019972-88-3(Hazardous Substances Data)

Upstream product

• 113181-02-5 (S)-(-)-3-bromo-2-hydroxy-2-methyl-N-[(4-cyano-3-(trifluoromethyl)phenyl)]propanamide 
• 654-70-6 4-amino-2-trifluoromethylbenzonitrile 
• 206193-17-1 (2R)-3-bromo-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methylpropanamide 

Downstream Products

• 850218-74-5 (S)-{4-[2-(4-cyano-3-trifluoromethylphenylcarbamoyl)-2-hydroxypropoxy]phenyl}carbamic acid tert-butyl ester 
• 2031161-35-8 (2R)-N-[4-cyano-3-(trifluoromethyl)phenyl]-3-(5-fluoro-1H-indol-1-yl)-2-hydroxy-2-methylpropanamide 
• 897364-32-8 (2S)-2-(tert-butyldimethylsilanyloxy)-N-(4-cyano-3-trifluoromethylphenyl)-3-(4-fluorophenoxy)-2-methylpropionamide 
• 911297-13-7 (S)-3-(4-amino-3-fluorophenoxy)-2-hydroxy-2-methyl-N-(4-cyano-3-trifluoromethylphenylcarbamoyl)propionamide 
• 850218-75-6 (S)-3-(4-aminophenoxy)-2-hydroxy-2-methyl-N-(4-cyano-3-trifluoromethylphenylcarbamoyl)propionamide 
• 541497-95-4 (2S)-N-(4-cyano-3-trifluoromethylphenyl)-3-(4-fluorophenoxy)-2-hydroxy-2-methylpropionamide 
• 911297-09-1 (S)-{4-[2-(4-cyano-3-trifluoromethylphenylcarbamoyl)-2-hydroxypropoxy]-2-fluorophenyl}carbamic acid tert-butyl ester 

Relevant articles and documents

Cesium fluoride and tetra-n-butylammonium fluoride mediated 1,4-N→O shift of disubstituted phenyl ring of a bicalutamide derivative

A novel 1,4-N→O migration of a disubstituted phenyl ring was observed during N-methylation of a bicalutamide derivative, (2S)-2-(tert-butyldimethylsilanyloxy)-N-(4-cyano-3-trifluoromethylphenyl)-3-(4-fluorophenoxy)-2-methylpropionamide, in the presence of

SELECTIVE ANDROGEN RECEPTOR DEGRADER (SARD) LIGANDS AND METHODS OF USE THEREOF

This invention provides novel indole, indazole, benzimidazole, indoline, quinolone, isoquinoline, and carbazole selective androgen receptor degrader (SARD) compounds, pharmaceutical compositions and uses thereof in treating prostate cancer, advanced prostate cancer, castration resistant prostate cancer, androgenic alopecia or other hyper androgenic dermal diseases, Kennedy's disease, amyotrophic lateral sclerosis (ALS), and uterine fibroids, and to methods for reducing the levels of androgen receptor-full length (AR-FL) including pathogenic and/or resistance mutations, AR-splice variants (AR-SV), and pathogenic polyglutamine (polyQ) polymorphisms of AR in a subject.

Arylisothiocyanato selective androgen receptor modulators (SARMs) for prostate cancer

A new series of androgen receptor targeted agents (ARTA) was prepared and tested in androgen-dependent and -independent prostate cancer cell lines. These agents were bicalutamide analogs with isothiocyanato substituted B-rings. Also, the linker sulfone of R-bicalutamide was maintained or replaced with several alternative linkages including ether, amine, N-methylamine, thioether, and methylene (in this case the product was a racemic mixture) functional groups at the X-position. To expand the structure-activity relationship (SAR) of these arylisothiocyanato AR ligands, B-ring halogenated arylisothiocyanato ligands were also prepared and tested. The arylisothiocyanato AR ligands showed strong binding affinities to AR ranging from 0.6 to 54 nM. Among them, thioether and ether linkages demonstrated high binding affinities (0.6 and 4.6 nM, respectively) and selective cell growth inhibition (approximately 3- to 6-fold) for LNCaP, an androgen-dependent prostate cancer cell line, when compared to the androgen independent prostate cell lines (DU145, PC-3, and PPC-1) and a bladder cell line (TSU-Pr1). However, the ligands were inactive (IC50>100 mM) in a normal monkey kidney cell line (CV-1) that was used as the control for non-specific toxicity.