170570-75-9

Basic information

• Product Name: Dehydroxy BroMocelecoxib
• Synonyms: Dehydroxy BroMocelecoxib
• CAS NO: 170570-75-9
• Molecular Formula: C₁₇H₁₃BrF₃N₃O₂S
• Molecular Weight: 460.27
• Product Categories: Amines, Aromatics, Heterocycles, Inhibitors, Pharmaceuticals, Intermediates & Fine Chemicals, Sulfur & Selenium Compounds
• Mol File: 170570-75-9.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Solubility: Chloroform, DCM
• CAS DataBase Reference: Dehydroxy BroMocelecoxib(CAS DataBase Reference)
• NIST Chemistry Reference: Dehydroxy BroMocelecoxib(170570-75-9)
• EPA Substance Registry System: Dehydroxy BroMocelecoxib(170570-75-9)

Safety Data

• Hazardous Substances Data: 170570-75-9(Hazardous Substances Data)

Usage

Uses

Dehydroxy Bromocelecoxib is an intermediate in the synthesis of Celecoxib (C251000), a selective cyclooxygenase-2 (COX-2) inhibitor with known anti-inflammatory properties.

Upstream product

• 122-00-9 para-methylacetophenone 
• 17852-52-7 4-hydrazinobenzene-1-sulfonamide hydrochloride 
• 720-94-5 4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione 
• 169590-42-5 4-[5-(4-(methyl)phenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulphonamide 

Downstream Products

• 170571-00-3 Methylhydroxy-Celecoxib 
• 169590-42-5 4-[5-(4-(methyl)phenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulphonamide 
• 1085712-46-4 C₂₅H₂₅F₃N₆O₈S 

Relevant articles and documents

Diazen-1-ium-1,2-diolated nitric oxide donor ester prodrugs of 5-(4-hydroxymethylphenyl)-1-(4-aminosulfonylphenyl)-3-trifluoromethyl-1H-pyrazole and its methanesulfonyl analog: Synthesis, biological evaluation and nitric oxide release studies

A new class of hybrid nitric oxide-releasing anti-inflammatory (AI) ester prodrugs (NONO-coxibs 12a-b) wherein an O2-acetoxymethyl 1-(2-carboxypyrrolidin-1-yl)diazen-1-ium-1,2-diolate (11, O2-acetoxymethyl PROLI/NO) NO-donor moiety was covalently coupled to the bromomethyl group of 5-(4-bromomethylphenyl)-1-(4-aminosulfonylphenyl)-3-trifluoromethyl-1H-pyrazole (9a), and its methanesulfonyl analog (9b), were synthesized. The diazen-1-ium-1,2-diolate compounds 12a-b released a low amount of NO upon incubation with phosphate buffer (PBS) at pH 7.4 (6.1-8.2% range). In comparison, the percentage NO released was significantly higher (76-77% of the theoretical maximal release of two molecules of NO/molecule of the parent hybrid ester prodrug) when the diazen-1-ium-1,2-diolate ester prodrugs 12a-b were incubated in the presence of rat serum. These incubation studies suggest that both NO and the anti-inflammatory 5-(4-hydroxymethylphenyl)-1-(4-aminosulfonylphenyl)-3-trifluoromethyl-1H-pyrazole (10a), and its methanesulfonyl analog (10b), would be released from the parent NONO-coxib 12a or 12b upon in vivo cleavage by non-specific serum esterases. The hydroxymethyl compounds 10a-b were weak inhibitors of the cyclooxygenase-1 (COX-1) and COX-2 isozymes (IC50 = 3.7-10.5 μM range). However, the hydroxymethyl compounds 10a-b and the parent NONO-coxibs 12a-b exhibited good AI activities (ED50 = 76.7-111.6 μmol/kg po range) that were greater than that exhibited by the reference drugs aspirin (ED50 = 710 μmol/kg po) and ibuprofen (ED50 = 327 μmol/kg po), but less than that of celecoxib (ED50 = 30.9 μmol/kg po). These studies indicate hybrid ester AI/NO-donor prodrugs (NONO-coxibs) constitutes a plausible drug design concept targeted toward the development of selective COX-2 inhibitory AI drugs that are devoid of adverse cardiovascular effects.