52209-61-7

Basic information

• Product Name: 4-isothiocyanato-1-nitro-2-(trifluoromethyl)benzene
• Synonyms: 4-isothiocyanato-1-nitro-2-(trifluoromethyl)benzene
• CAS NO: 52209-61-7
• Molecular Weight: 248.185
• Mol File: 52209-61-7.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: 4-isothiocyanato-1-nitro-2-(trifluoromethyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-isothiocyanato-1-nitro-2-(trifluoromethyl)benzene(52209-61-7)
• EPA Substance Registry System: 4-isothiocyanato-1-nitro-2-(trifluoromethyl)benzene(52209-61-7)

Safety Data

• Hazardous Substances Data: 52209-61-7(Hazardous Substances Data)

Upstream product

• 463-71-8 thiophosgene 
• 393-11-3 4-nitro-3-(trifluoromethyl)benzeneamine 

Downstream Products

• 1003838-45-6 C₁₁H₈F₃N₃O₃S 
• 1214896-22-6 1-benzyl-3-(4-nitro-3-(trifluoromethyl)phenyl)-2-thioxotetrahydropyrimidin-4(1H)-one 
• 1214896-36-2 1-ethyl-3-(4-nitro-3-(trifluoromethyl)phenyl)-2-thioxotetrahydropyrimidin-4(1H)-one 
• 1214896-10-2 3-(4-nitro-3-(trifluoromethyl)phenyl)-1-(1-phenylethyl)-2-thioxotetrahydropyrimidin-4(1H)-one 
• 1315245-48-7 tert-butyl 3-(4-nitro-3-trifluoromethylphenyl)-5-methyl-4-oxo-2-thioxoimidazolidine-1-carboxylate 
• 1315245-42-1 5-methyl-3-(4-nitro-3-(trifluoromethyl)phenyl)-4-oxo-2-thioxoimidazolidine 

Relevant articles and documents

A new series of bicalutamide, enzalutamide and enobosarm derivatives carrying pentafluorosulfanyl (SF5) and pentafluoroethyl (C2F5) substituents: Improved antiproliferative agents against prostate cancer

SAR studies on bicalutamide, enobosarm and enzalutamide analogues, functionalised with polyfluorinated groups, is presented. Among the novel bicalutamide and enobosarm derivatives synthesised, several displayed significantly improved in vitro anticancer activity, with IC50 values in the low micromolar range against four different prostate cancer cell lines (LNCaP, VCaP, DU-145 and 22Rv1), showing up to 48-fold increase in comparison with the parent structures. In particular, SF5 enobosarm analogues were found to be most potent compounds, full AR antagonists and with favourable ADME properties. The most promising compound (48a) was evaluated for its in vivo efficacy in PC xenograft mouse model (22Rv1) with results comparable to the standard-of-care docetaxel.

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.

ANDROGEN RECEPTOR MODULATORS AND THEIR USE AS ANTI-CANCER AGENTS

Compounds having therapeutic potential as androgen receptor modulators and anti- cancer agents, and methods of making such compounds, are provided. The compounds are structurally related to bicalutamide, enobosarm and enzalutamide, but bear a 3,5-bis- CF