189500-90-1

Basic information

• Product Name: 1-(4-FLUOROPHENYL)-2-METHYL-5-[4-(METHYLSULFONYL)PHENYL]-1H-PYRROLE
• Synonyms: 1-(4-FLUOROPHENYL)-2-METHYL-5-[4-(METHYLSULFONYL)PHENYL]-1H-PYRROLE;4-[1-(4-FLUOROPHENYL)-5-METHYL-1H-PYRROL-2-YL]PHENYL METHYL SULFONE;1-(4-fluorophenyl)-2-(4-methanesulfonylphenyl)-5-methyl-1H-pyrrole
• CAS NO: 189500-90-1
• Molecular Formula: C₁₈H₁₆FNO₂S
• Molecular Weight: 329.39
• Mol File: 189500-90-1.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(4-FLUOROPHENYL)-2-METHYL-5-[4-(METHYLSULFONYL)PHENYL]-1H-PYRROLE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-FLUOROPHENYL)-2-METHYL-5-[4-(METHYLSULFONYL)PHENYL]-1H-PYRROLE(189500-90-1)
• EPA Substance Registry System: 1-(4-FLUOROPHENYL)-2-METHYL-5-[4-(METHYLSULFONYL)PHENYL]-1H-PYRROLE(189500-90-1)

Safety Data

• Hazardous Substances Data: 189500-90-1(Hazardous Substances Data)

Upstream product

• 5398-77-6 para-methanesulfonylbenzaldehyde 
• 3446-89-7 4-(Methylthio)benzaldehyde 
• 371-40-4 4-fluoroaniline 
• 189501-34-6 1-[4-(methylsulfonyl)phenyl]pentane-1,4-dione 
• 189501-33-5 1-[4-(methylthio)phenyl]pentane-1,4-dione 

Downstream Products

• 189501-17-5 2,2,2-trifluoro-1-[1-(4-fluorophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrol-3-yl]ethanone 
• 1442652-35-8 2-methyl-5-[4-(methylsulfonyl)phenyl]-1-[4-fluorophenyl]-1H-pyrrole-3-carboxime 
• 1363374-20-2 4-(nitrooxy)butyl-[2-amino-2-[1-(4-fluorophenyl)-2-methyl-5-(4-methylsulphonylphenyl)-1H-pyrrol-3-yl]]-acetate 
• 1363374-15-5 3-(nitrooxy)propyl-[2-amino-2-[1-(4-fluorophenyl)-2-methyl-5-(4-methylsulphonylphenyl)-1H-pyrrol-3-yl]]-acetate 
• 1363374-95-1 4-(hydroxy)butyl-[2-amino-2-[1-(4-fluorophenyl)-2-methyl-5-(4-methylsulphonyl phenyl)-1H-pyrrol-3-yl]]-acetate 
• 1363374-91-7 3-(hydroxy)propyl-[2-amino-2-[1-(4-fluorophenyl)-2-methyl-5-(4-methylsulphonyl phenyl)-1H-pyrrol-3-yl]]-acetate 
• 1415910-89-2 4-(nitrooxy)butyl N-((benzyloxy)carbonyl)-2-[1-(4-fluorophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrol-3-yl]-2-amino-acetate 
• 1415910-87-0 3-(nitrooxy)propyl N-((benzyloxy)carbonyl)-2-[1-(4-fluorophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrol-3-yl]-2-amino-acetate 
• 1415910-85-8 4-(nitrooxy)butyl N-(tert-butoxycarbonyl)-2-(1-(4-fluorophenyl)-2-methyl-5-(4-(methylsulfonyl)phenyl)-1H-pyrrol-3-yl)-2-amino-acetate 
• 1415910-83-6 3-(nitrooxy)propyl N-(tert-butoxycarbonyl)-2-(1-(4-fluorophenyl)-2-methyl-5-(4-(methylsulfonyl)phenyl)-1H-pyrrol-3-yl)-2-amino-acetate 
• 1415910-81-4 N-(tert-butoxycarbonyl)-2-[1-(4-fluorophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrol-3-yl]-2-amino-acetic acid 
• 1363375-42-1 ethyl 2-hydroxy-imino-2-[1-(4-fluorophenyl)-2-methyl-5-(4-methylsulphonylphenyl)-1H-pyrrol-3-yl]-acetate 
• 1363375-96-5 benzyl N-((ethoxycarbonyl)-[1-(4-fluorophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrol-3-yl]methyl)carbamate 
• 1363375-41-0 ethyl [2-amino-2-[1-(4-fluorophenyl)-2-methyl-5-(4-methanesulphonylphenyl)-1H-pyrrol-3-yl]]-acetate 

Relevant articles and documents

A fluorescent target-guided Paal-Knorr reaction

It has become increasingly apparent that high-diversity chemical reactions play a significant role in the discovery of bioactive small molecules. Here, we describe an expanse of this paradigm, combining a ‘target-guided synthesis’ concept with Paal-Knorr chemistry applied to the preparation of fluorescent ligands for human prostaglandin-endoperoxide synthase (COX-2).

Improving the solubility of a new class of antiinflammatory pharmacodynamic hybrids, that release nitric oxide and inhibit cycloxygenase-2 isoenzyme

The development of a novel class of pharmacodynamic hybrids that inhibits COX-2 isoform is reported. These molecules display enhanced nitric oxide releasing properties due to the presence of an ionisable moiety. The in vivo analgesic/anti-inflammatory activity was maintained in relation to the parent compounds.

Cyclooxygenase-2 inhibitors. 1,5-diarylpyrrol-3-acetic esters with enhanced inhibitory activity toward cyclooxygenase-2 and improved cyclooxygenase-2/ cyclooxygenase-1 selectivity

The important role of cyclooxygenase-2 (COX-2) in the pathogenesis of inflammation and side effect limitations of current COX-2 inhibitor drugs illustrates a need for the design of new compounds based on alternative structural templates. We previously reported a set of substituted 1,5-diarylpyrrole derivatives, along with their inhibitory activity toward COX enzymes. Several compounds proved to be highly selective COX-2 inhibitors and their affinity data were rationalized through docking simulations. In this paper, we describe the synthesis of new 1,5-diarylpyrrole derivatives that were assayed for their in vitro inhibitory effects toward COX isozymes. Among them, the ethyl-2-methyl-5-[4-(methylsulfonyl)phenyl]-1-[3-fluorophenyl]-1H-pyrrol-3- acetate (1d), which was the most potent and COX-2 selective compound, also showed a very interesting in vivo anti-inflammatory and analgesic activity, laying the foundations for developing new lead compounds that could be effective agents in the armamentarium for the management of inflammation and pain.