90356-80-2

Basic information

• Product Name: N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methyl-3-(pyridin-2-ylthio)propanamide
• Synonyms: N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methyl-3-(pyridin-2-ylthio)propanamide
• CAS NO: 90356-80-2
• Molecular Weight: 381.378
• Mol File: 90356-80-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methyl-3-(pyridin-2-ylthio)propanamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methyl-3-(pyridin-2-ylthio)propanamide(90356-80-2)
• EPA Substance Registry System: N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methyl-3-(pyridin-2-ylthio)propanamide(90356-80-2)

Safety Data

• Hazardous Substances Data: 90356-80-2(Hazardous Substances Data)

Upstream product

• 90357-53-2 N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methylacrylamide 
• 654-70-6 4-amino-2-trifluoromethylbenzonitrile 
• 2637-34-5 2-Sulfanylpyridine 
• 90357-51-0 N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methyloxirane-2-carboxamide 

Relevant articles and documents

Synthesis, biological evaluation and X-ray analysis of bicalutamide sulfoxide analogues for the potential treatment of prostate cancer

The androgen receptor (AR) is a pivotal target for the treatment of prostate cancer (PC) even when the disease progresses toward androgen-independent or castration-resistant forms. In this study, a series of sulfoxide derivatives were prepared and their antiproliferative activity evaluated in vitro against four different human prostate cancer cell lines (22Rv1, DU-145, LNCaP and VCap). Bicalutamide and enzalutamide were used as positive controls. Compound 28 displayed significant enhancement in anticancer activity across the four PC cell lines with IC50 = 9.09 – 31.11 μM compared to the positive controls: bicalutamide (IC50 = 45.20 –51.61 μM) and enzalutamide (IC50 = 11.47 – 53.04 μM). Sulfoxide derivatives of bicalutamide were prepared efficiently from the corresponding sulfides using only one equivalent of mCPBA, limiting the reaction time to 15–30 min and maintaining the temperature at 0 °C. Interestingly, three pairs of sulfoxide diastereomers were separated and NMR comparison of their diastereotopic methylene (CH2) group is presented. X-ray diffraction crystal structure analysis provided relative configuration assignment at the chiral sulfur and carbon centres. Molecular modelling study of the four diastereoisomers of compound 28 is described.

Nonsteroidal antiandrogens. Synthesis and structure-activity relationship of 3-substituted derivatives of 2-hydroxypropionanilides

A series of 3-(substituted thio)-2-hydroxypropionanilides and some corresponding sulfones and sulfoxides of general structure 7, in which R' is methyl or trifluoromethyl, were prepared and tested for antiandrogen activity. Members of the trifluoromethyl series (7,R' = CF3) generally exhibited partial androgen agonist activity whereas the members of the methyl series (7,R' = CH3) were pure antagonists. Lead optimization in the methyl series has led to the discovery of novel, potent antiandrogens, which are peripherally selective. One of these, (RS)-4'-cyano-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methyl-3'-(trifd luoromethyl)propionanilide, 40 (ICI 176334), is being developed currently for the treatment of androgen-responsive benign and malignant disease.