170569-91-2

Basic information

• Product Name: Benzenesulfonamide, 4-[5-(4-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]-
• CAS NO: 170569-91-2
• Molecular Formula: C17H14F3N3O3S
• Molecular Weight: 397.378
• Mol File: 170569-91-2.mol
• Article Data: 29

Chemical Properties

• CAS DataBase Reference: Benzenesulfonamide, 4-[5-(4-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfonamide, 4-[5-(4-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]-(170569-91-2)
• EPA Substance Registry System: Benzenesulfonamide, 4-[5-(4-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]-(170569-91-2)

Safety Data

• Hazardous Substances Data: 170569-91-2(Hazardous Substances Data)

Upstream product

• 15191-68-1 4,4,4-trifluoro-1-(4-methoxyphenyl)-1,3-butanedione 
• 4392-54-5 4-aminosulfonylphenylhydrazine 
• 170569-87-6 4-(5-phenyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzenesulfonamide 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 17852-52-7 4-hydrazinobenzene-1-sulfonamide hydrochloride 
• 910303-55-8 (Z)-1,1,1-trifluoro-4-hydroxy-4-(4-methoxyphenyl)but-3-en-2-one 
• 415944-56-8 (p-methoxybenzoyl)trifluoroacetonate 

Relevant articles and documents

A CONTINUOUS FLOW MICRO-TOTAL PROCESS SYSTEM FOR PREPARATION OF CELECOXIB AND ANALOGS THEREOF

The present invention relates to preparation of pyrazoles. This invention further relates to a continuous flow micro-total process system for preparation of celecoxib, a COX-2 selective non-steroidal anti-inflammatory drug, and analogs thereof.

Synthesis of 1,5-diarylpyrazoles as potential cox-2 inhibitors with nitric oxide releasing ability

A few celecosib like 1,5-diarylpyrazoles conjugated with nitric oxide (NO) donating nitrate ester group were synthesized and evaluated for their selective COX-2 inhibitory activity along with NO releasing ability of corresponding nitrate esters. Most of the synthesized compounds exhibited improved COX-2 inhibition when compared with the reference drug celecoxib. The nitrate ester derivatives (coxib prodrugs) 7 (nitrate ester of 1,5-diarylpyrazole with 2 carbon linker), and 9 (nitrate ester of 1,5-diarylpyrazole with 3 carbon linker), upon incubation in human whole blood were partly transformed into the corresponding alcohols 6, and 8 respectively. Molecular docking studies were performed on alcohol derivatives and revealed additional H-bond interactions compared to celecoxib.

Synthesis and preliminary in vitro biological evaluation of new carbon-11-labeled celecoxib derivatives as candidate PET tracers for imaging of COX-2 expression in cancer

The enzyme cyclooxygenase-2 (COX-2) is overexpressed in a variety of malignant tumors. This study was designed to develop new radiotracers for imaging of COX-2 in cancer using biomedical imaging technique positron emission tomography (PET). Carbon-11-labeled celecoxib derivatives, [11C]4a-c and [11C]8a-d, were prepared by O-[11C] methylation of their corresponding precursors using [11C]CH3OTf under basic conditions and isolated by a simplified solid-phase extraction (SPE) method in 52 ± 2% (n = 5) and 57 ± 3% (n = 5) radiochemical yields based on [11C]CO2 and decay corrected to end of bombardment (EOB). The overall synthesis time from EOB was 23 min, the radiochemical purity was >99%, and the specific activity at end of synthesis (EOS) was 277.5 ± 92.5 GBq/μmol (n = 5). The IC50 values to block COX-2 for known compounds celecoxib (4d), 4a and 4c were 40, 290 and 8 nM, respectively, and preliminary findings from in vitro biological assay indicated that the synthesized new compounds 4b and 8a-d display similar strong inhibitory effectiveness in the MDA-MB-435 human cancer cell line in comparison with the parent compound 4d. These results encourage further in vivo evaluation of carbon-11-labeled celecoxib derivatives as new potential PET radiotracers for imaging of COX-2 expression in cancer.