301692-76-2

Basic information

• Product Name: 4-(3-(3-fluorophenyl)-5,5-dimethyl-4-oxo-4,5-dihydrofuran-2-yl)benzenesulfonamide
• Synonyms: 4-(3-(3-fluorophenyl)-5,5-dimethyl-4-oxo-4,5-dihydrofuran-2-yl)benzenesulfonamide;4-[3-(3-fluorophenyl)-5,5-diMethyl-4-oxo-4,5-dihydrofuran-2-yl]benzene-1-sulfonaMide;Polmacoxib
• CAS NO: 301692-76-2
• Molecular Formula: C₁₈H₁₆FNO₄S
• Molecular Weight: 361
• Mol File: 301692-76-2.mol

Chemical Properties

• Melting Point: 155-156 °C
• Boiling Point: 527.7±60.0 °C(Predicted)
• Appearance: /
• Density: 1.361±0.06 g/cm3(Predicted)
• PKA: 10.21±0.10(Predicted)
• CAS DataBase Reference: 4-(3-(3-fluorophenyl)-5,5-dimethyl-4-oxo-4,5-dihydrofuran-2-yl)benzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(3-(3-fluorophenyl)-5,5-dimethyl-4-oxo-4,5-dihydrofuran-2-yl)benzenesulfonamide(301692-76-2)
• EPA Substance Registry System: 4-(3-(3-fluorophenyl)-5,5-dimethyl-4-oxo-4,5-dihydrofuran-2-yl)benzenesulfonamide(301692-76-2)

Safety Data

• Hazardous Substances Data: 301692-76-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-(3-(3-fluorophenyl)-5,5-dimethyl-4-oxo-4,5-dihydrofuran-2-yl)benzenesulfonamide is used as a pharmaceutical compound for its potential therapeutic effects. The molecule's unique structure allows it to interact with specific biological targets, making it a promising candidate for the development of new drugs. Its application in this industry is driven by the need for novel therapeutic agents with improved efficacy and safety profiles.
Used in Chemical Research:
In the field of chemical research, 4-(3-(3-fluorophenyl)-5,5-dimethyl-4-oxo-4,5-dihydrofuran-2-yl)benzenesulfonamide serves as a valuable compound for studying various chemical reactions and mechanisms. Its structural features provide opportunities for further modification and functionalization, which can lead to the discovery of new compounds with enhanced properties and applications.
Used in Material Science:
The unique structural features of 4-(3-(3-fluorophenyl)-5,5-dimethyl-4-oxo-4,5-dihydrofuran-2-yl)benzenesulfonamide also make it a candidate for applications in material science. Its potential use in the development of new materials with specific properties, such as improved stability, reactivity, or selectivity, can be explored. This application is driven by the need for innovative materials that can address various challenges in different industries.

Biochem/physiol Actions

Polmacoxib is a nonsteroidal anti-inflammatory drug (NSAID) that acts as an inhibitor of cyclooxygenase 2 (COX-2) and the carbonic anhydrases CAI and CAII. It has also been found to inhibit colorectal adenoma and tumor growth in mouse models.

Synthesis

Subjection of commercial propargyl alcohol 172 to nbutyllithium at cryogenic temperatures followed by quenching with commercial benzaldehyde 173 resulted in the formation of benzyl alcohol 174 in 81% yield. This alcohol could be oxidized by three different means, but the authors report that the most suitable method on scale was through the use of manganese dioxide in methylene chloride, which furnished ketone 175 in 80%. Next, an interesting cyclization reaction secured the key furanone residue 176. Mechanistically, subjection of ynone 175 to dimethylamine likely resulted in a conjugate addition followed by tautomerization of the resulting allenol to the corresponding ketone. The resulting ketone then probably underwent intramolecular nucleophilic attack by the pendant tertiary alcohol and after ejection of a molecule of water through iminium-mediated lone pair assistance, hydrolysis of the iminium species to the corresponding ketone delivered 176. Next, mCPBA was employed to oxidize sulfide 176 to the corresponding sulfoxide. Subsequently, iodination of the furanone through use of bis(trifluoroacetoxy)iodobenzene (BTI), followed by a three-step sequence to convert the methylsulfoxide to the corresponding primary sulfonamide 178 occurred in 41% overall from the four-step sequence. Finally, Suzuki installation of the fluorobenzene resulted in the completion of the synthesis of polmacoxib (XXII).

Upstream product

• 768-35-4 3-fluorophenylboronic acid 
• 301699-02-5 5-{4-(aminosulfonyl)phenyl}-2,2-dimethyl-4-iodo-3(2H)furanone 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 3446-89-7 4-(Methylthio)benzaldehyde 
• 301698-95-3 2,2-dimethyl-5-(4-(methylthio)phenyl)-3(2H)furanone 
• 301698-93-1 1-{4-(methylthio)phenyl}-4-hydroxy-4-methyl-2-pentyn-1-ol 
• 301698-94-2 1-{4-(methylthio)phenyl}-4-hydroxy-4-methyl-2-pentyn-1-one 
• 301699-00-3 2,2-dimethyl-5-{4-(methylsulfinyl)phenyl}-3(2H)furanone 
• 301699-01-4 2,2-dimethyl-4-iodo-5-{4-(methylsulfinyl)phenyl}-3(2H)furanone 

Downstream Products

• 301693-84-5 5-[4-{(Butyrylamino)sulfonyl}phenyl]-2,2-dimethyl-4-(3-fluorophenyl)-3(2H)-furanone 
• 301693-82-3 5-[4-{(Acetylamino)sulfonyl}phenyl]-2,2-dimethyl-4-(3-fluorophenyl)-3(2H)-furanone 

Relevant articles and documents

Method for producing polmacoxib

The present invention relates to a method for preparing polmacoxib used as a medicine for treating osteoarthritis. The method for preparing polmacoxib includes a step of reacting a sufinate compound represented by chemical formula 2 with a hydroxylamine-O-sulfonic acid (HOSA) to obtain polmacoxib represented by chemical formula 1.COPYRIGHT KIPO 2021

In Vitro Structure-Activity Relationship and in Vivo Studies for a Novel Class of Cyclooxygenase-2 Inhibitors: 5-Aryl-2,2-dialkyl-4-phenyl-3(2H)furanone Derivatives

5-Aryl-2,2-dialkyl-4-phenyl-3(2H)furanone derivatives were studied as a novel class of selective cyclooxygenase-2 inhibitors with regard to synthesis, in vitro SAR, antiinflammatory activities, pharmacokinetic considerations, and gastric safety. If, a representative compound for methyl sulfone derivatives, showed a COX-2 IC50 comparable to that of rofecoxib. In case of 20b, a representative compound for sulfonamide derivatives, a potent antiinflammatory ED50 of 0.1 mg kg-1 day-1 was observed against adjuvant-induced arthritis by a preventive model, positioning 20b as one of the most potent COX-2 inhibitors ever reported. Furthermore, 20b showed strong analgesic activity as indicated by its ED50 of 0.25 mg/kg against carrageenan-induced thermal hyperalgesia in the Sprague-Dawley rat. 3(2H)Furanone derivatives showed due gastric safety profiles as selective COX-2 inhibitors upon 7-day repeat dosing. A highly potent COX-2 inhibitor of the 3(2H)furanone scaffold could be considered suitable for a future generation COX-2 selective arthritis medication with improved safety profiles.