90356-78-8

Basic information

• Product Name: N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)thio]-2-hydroxy-2-methylpropionamide
• Synonyms: (R,S)-N-[4-Cyano-3-(trifluoroMethyl)phenyl]-3-[(4-fluorophenyl)thio]-2-hydroxy-2-MethylpropionaMide;N-[4-Cyano-3-(TrifluoroMethyl)Phenyl]-3-[(4-Fluorophenyl)thio]-2-Hydroxy-2-Methy-PropanaMide;N-[4-Cyano-3-trifluoroMethy phenyl]-S-(4-fluorophenylthio)-2-hydrdoxy-2-Methyl-propionaMide(ASH BicalutaMide);N-[4-cyano-3-(rifluoromethyl)phenyl]-3-[(4-fluorophenyl)thio]-2- hydroxy-2-methyl propan Amide;90356-78-8;Bicalutamide EP Impurity J;N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)thio]-2-hydroxy-2-methylpropiomide;4-CYANO-3-TRIFLUOROMETHYL-N-[3-(4-FLUOROPHENYLTHIO)-2-HYDROXYL-2-METHYLPROPIONYL]ANILINE
• CAS NO: 90356-78-8
• Molecular Formula: C₁₈H₁₄F₄N₂O₂S
• Molecular Weight: 398.37
• EINECS: 1312995-182-4
• Product Categories: (intermediate of bicalutamide);Bicalutamide;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 90356-78-8.mol
• Article Data: 20

Chemical Properties

• Melting Point: 109-111°C
• Boiling Point: 565.588 °C at 760 mmHg
• Flash Point: 295.857 °C
• Appearance: off-white crystalline powder
• Density: 1.43 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.585
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 12.31±0.29(Predicted)
• CAS DataBase Reference: N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)thio]-2-hydroxy-2-methylpropionamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)thio]-2-hydroxy-2-methylpropionamide(90356-78-8)
• EPA Substance Registry System: N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)thio]-2-hydroxy-2-methylpropionamide(90356-78-8)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 90356-78-8(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Bicalutamide intermediate.

InChI:InChI=1/C18H14F4N2O2S/c1-17(26,10-27-14-6-3-12(19)4-7-14)16(25)24-13-5-2-11(9-23)15(8-13)18(20,21)22/h2-8,26H,10H2,1H3,(H,24,25)

Upstream product

• 6293-83-0 2-iodo-4-nitrophenylamine 
• 300627-43-4 2-iodo-4-nitrobenzonitrile 
• 540-51-2 2-bromoethanol 
• 300627-48-9 4-amino-2-iodobenzonitrile 
• 371-42-6 4-Fluorothiophenol 
• 90357-53-2 N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methylacrylamide 
• 35337-66-7 4-fluorobenzenethiolate 
• 90357-51-0 N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methyloxirane-2-carboxamide 
• 3887-61-4 sodium 4-fluorophenylthiolate 
• 316373-95-2 N-[4-cyano-3-trifluoromethyl-phenyl]-2-hydroxy-3-methanesulfonyloxy-2-methyl-propionamide 
• 7440-44-0 pyrographite 
• 339530-91-5 3-(4-Fluoro-phenylsulfanyl)-2-hydroxy-2-methyl-propionic acid 
• 654-70-6 4-amino-2-trifluoromethylbenzonitrile 
• 873014-32-5 N-[4-cyano-3-(trifluoromethyl)-phenyl-]-3-[4-fluorophenylthio]-2-acetoxy-2-methyl-propionamide 

Downstream Products

• 945419-64-7 N-[4-cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorophenyl)sulfinyl-2-hydroxy-2-methyl-propanamide 
• 90357-06-5 Bicalutamide 
• 113299-39-1 4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid 1-(4-cyano-3-trifluoromethyl-phenylcarbamoyl)-2-(4-fluoro-phenylsulfanyl)-1-methyl-ethyl ester 

Relevant articles and documents

Nucleophilic Aromatic Substitution of Methacrylamide Anion and Its Application to the Synthesis of the Anticancer Drug Bicalutamide

The anticancer drug (R,S)-biscaltamide was prepared in three steps in >90% overall yield. A key step in the new synthesis involved a new nucleophilic aromatic substitution reaction of methacrylamide anion.

Preparation method of bicalutamide thioether intermediate

The invention relates to a preparation method of a bicalutamide thioether intermediate, and relates to the synthesis of chemical drugs, in particular to a preparation method of N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[4-fluorophenylthio]-2-hydroxy-2-methylpropionamide. According to the method, a lower fatty acid ester is taken as a solvent, an alkali metal salt of a lower aliphatic alcohol is taken as a catalyst, 4-fluorothiophenol first reacts with the alkali metal salt of the lower aliphatic alcohol to generate 4-fluorfenthiolate, then N-[4-cyano-3-(trifluoromethyl)phenyl]-1,2-epoxy-2-methylpropionamide is added into 4-fluorfenthiolate for a reaction at room temperature, and a finished product is obtained after separation and purification. The preparation method provided by the inventionis mild in reaction conditions, the use of high-risk sodium hydride and expensive tetrahydrofuran is avoided, and a reaction solvent can also be recycled and reused, thereby reducing cost and reducing emissions.

Design and synthesis of novel bicalutamide and enzalutamide derivatives as antiproliferative agents for the treatment of prostate cancer

Prostate cancer (PC) is one of the major causes of male death worldwide and the development of new and more potent anti-PC compounds is a constant requirement. Among the current treatments, (R)-bicalutamide and enzalutamide are non-steroidal androgen receptor antagonist drugs approved also in the case of castration-resistant forms. Both these drugs present a moderate antiproliferative activity and their use is limited due to the development of resistant mutants of their biological target. Insertion of fluorinated and perfluorinated groups in biologically active compounds is a current trend in medicinal chemistry, applied to improve their efficacy and stability profiles. As a means to obtain such effects, different modifications with perfluoro groups were rationally designed on the bicalutamide and enzalutamide structures, leading to the synthesis of a series of new antiproliferative compounds. Several new analogues displayed improved in vitro activity towards four different prostate cancer cell lines, while maintaining full AR antagonism and therefore representing promising leads for further development. Furthermore, a series of molecular modelling studies were performed on the AR antagonist conformation, providing useful insights on potential protein-ligand interactions.