87483-29-2

Upstream product

• 21382-98-9 p-cyanophenyl methyl sulfide 
• 459-46-1 4-Fluorobenzyl bromide 
• 100-68-5 methyl-phenyl-thioether 
• 405-50-5 p-Fluorophenylacetic acid 
• 459-04-1 4-Fluorophenylacetyl chloride 

Downstream Products

• 175676-88-7 (E)-3-Dimethylamino-2-(4-fluoro-phenyl)-1-(4-methylsulfanyl-phenyl)-propenone 
• 165252-27-7 2-(4-fluorophenyl)-1-[4-(methylthio)phenyl]-4,4,4-trifluoro-1,3-butanedione 
• 329076-60-0 ethyl 2-(4-fluorophenyl)-2-((4-methylthio)benzoyl)acetic acid ethyl ester 
• 157671-97-1 4-fluoro-4'-(methylsulfonyl)benzil 
• 1027835-28-4 5-(4-fluoro-phenyl)-6-(4-methanesulfonyl-phenyl)-2,3-dihydro-pyrazine 
• 1059192-88-9 4-(4-fluoro-phenyl)-5-(4-methylsulfanyl-phenyl)-1H-pyrazol-3-ylamine 
• 328554-41-2 3-(4-fluoro-phenyl)-6,7-dimethyl-2-(4-methylsulfanyl-phenyl)-pyrazolo[1,5-a]pyrimidine 
• 328554-42-3 3-(4-fluorophenyl)-6,7-dimethyl-2-(4-methylsulfinylphenyl)pyrazolo[1,5-a]pyrimidine 
• 1027967-68-5 2-[4-(acetoxymethylthio)phenyl]-3-(4-fluorophenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidine 
• 1135071-45-2 2-(4-fluorophenyl)-1-(4-(methylthio)phenyl)propan-1-one 
• 1455276-57-9 4-(4-methylthiophenyl)-5-(4-fluorophenyl)-2-(benzylthio)-thiazole 
• 1542256-70-1 C₁₆H₁₂FN₃O₂S₂ 
• 1542256-65-4 C₁₅H₁₂FNO₄S 
• 1542256-75-6 5-(4-fluorophenyl)-6-(4-(methylsulfonyl)phenyl)-3-(methylthio)-1,2,4-triazine 

Relevant academic research and scientific papers

Synthesis and antiseizure activity of (E)-1,2-diarylethylidenehydrazine carboximidamides against tonic-clonic seizures: an intracerebroventricular and electrophysiological study

A series of (E)-1,2-diarylethylidenehydrazine carboximidamides 2a–j were synthesized and characterized by NOESY experiment as anticonvulsant agents and their antiseizure activity was evaluated by intracerebroventricular administration of compounds. Most of the compounds had significant protection against tonic-clonic seizures and 2a was found to be as equipotent as carbamazepine in seizures control. In order to find their anticonvulsant mechanism of action, 2a was subjected to further electrophysiological studies using patch-clamp technique. The results confirmed that this compound is neither a voltage-gated sodium channel blocker nor a NMDA/AMPA antagonist. Although 2a did not show any direct GABA agonistic activity, it could decrease EPSP and increase IPSP frequency without any change in amplitude. Finally, the results indicated most likely a presynaptic GABA-mediated mechanism of 2a for its antiseizure activity such as inhibition of the GABA-T which was validated by molecular docking.

Design, synthesis and in vitro study of 5,6-diaryl-1,2,4-triazine-3-ylthioacetate derivatives as COX-2 and β-amyloid aggregation inhibitors

In order to find novel cyclooxygenase (COX)-2 inhibitors for treating inflammatory-based diseases such as Alzheimer's disease (AD), an ethyl carboxylate side chain was added to 5-(4-chlorophenyl)-6-(4-(methylsulfonyl)phenyl)-3-(methylthio)-1,2,4-triazine

Synthesis, docking simulation, biological evaluations and 3D-QSAR study of 5-Aryl-6-(4-methylsulfonyl)-3-(metylthio)-1,2,4-triazine as selective cyclooxygenase-2 inhibitors

A series of 5-Aryl-6-(4-methylsulfonyl)-3-(metylthio)-1,2,4-triazine derivatives were synthesized and their COX-1/COX-2 inhibitory activity as well as in vivo anti-inflammatory and analgesic effects were evaluated. All of compounds showed strong inhibitio

Synthesis, cytotoxic evaluation, and molecular docking study of 4,5-diaryl-thiazole-2-thione analogs of combretastatin A-4 as microtubule-binding agents

A series of combretastatin A-4 analogs in which cis-olefinic bond replaced by thiazole ring were prepared by reaction of α-bromo-1,2-(p-substituted) diaryl-1-ethanones and dithiocarbamate derivatives. The cytotoxicity of these compounds was determined against three cancer cell lines (HT-29), (MCF-7), (AGS) as well as fibroblastic cell line (NIH-3T3) using MTT assay. Inhibition of tubulin polymerization for some potent compounds was evaluated. These biological studies proved that 6j and 6o were the most potent compounds in this series. Furthermore 2-(methylthio)-substituted compounds show moderate or no activity. Docking studies involving 6j and 6o demonstrated that this analogs could be successfully docked in the colchicine binding site of α,β-tubulin.

Synthesis, cyclooxygenase inhibitory effects, and molecular modeling study of 4-aryl-5-(4-(methylsulfonyl)phenyl)-2-alkylthio and -2-alkylsulfonyl-1H- imidazole derivatives

A series of 4-aryl-5-(4-(methylsulfonyl)phenyl)-2-alkylthio and 2-alkylsulfonyl-1H-imidazole derivatives were synthesized. All compounds were tested in human blood assay to determine COX-1 and COX-2 inhibitory potency and selectivity. Among the synthesize

Convenient and regiospecific method for synthesis of 4,5-diaryl-1-methyl-2- (methylthio)-1H-imidazole

A convenient, high-yielding, regiospecific synthesis of 1H-imidazole-2-thiones ring has been developed. In addition, a series of 4,5-diaryl-1-methyl-2-(methylthio)-1H-imidazoles 8 were synthesized and characterized. The structure of regioisomers was confirmed through nuclear Overhauser effect spectroscopy and NMR spectroscopy. Copyright

Diaryl-dithiolanes and -isothiazoles: COX-1/COX-2 and 5-LOX-inhibitory, {radical dot}OH scavenging and anti-adhesive activities

Three series of non-steroidal anti-inflammatory drugs (NSAIDs) inhibiting the cyclooxygenase/5-lipoxygenase (COX/5-LOX) pathways as such as formation of hydroxyl radicals and adhesion were prepared: 4,5-diaryl isothiazoles, 4,5-diaryl 3H-1,2-dithiole-3-thiones and 4,5-diaryl 3H-1,2-dithiole-3-ones. The aim of the present study was to develop substances which can intervene into the inflammatory processes via different mechanisms of action as multiple target non-steroidal anti-inflammatory drugs (MTNSAIDs) with increased anti-inflammatory potential. The current lead 11a was evaluated in COX-1/2, 5-LOX and {radical dot}OH scavenging in vitro assays and in a static adhesion assay where it proved to inhibit adhesion. Moreover, 11a treatment attenuated expression of macrophage adhesion molecule-1 (Mac-1) on extravasated polymorphonuclear leukocytes (PMNs) which indicates that the activation was reduced. The assays used are predictive for the in vivo efficacy of test compounds as shown for 11a in a peritonitis model of acute inflammation in mice. Thus, the novel 5-LOX/COX and {radical dot}OH inhibitor 11a possesses anti-inflammatory activity that, in addition to COX/5-LOX inhibition, implicates effects on leukocyte-endothelial interactions.

Syntheses of 4,5-diaryl-1,2,3-thiadiazoles

Reaction of thionyl chloride with semicarbazones of 1-(4- methylsulfonylphenyl)-2-(4-substituted pheny)lethanone gave 4-(4- methylsulfonylphenyl)-5-(4-substituted) pheny-1,2,3-thiadiazoles 5. Compounds 5-phenyl-4-(substitutedphenyl)-1,2,3-thiadiazoles 14 were similarly prepared. Chlorosulfonation of the latter followed by ammonia gave the desired compounds 5-(4-aminosulfonylphenyl)-4-(substituted) phenyl-1,2,3-thiadiazoles 6. Copyright Taylor & Francis Inc.

Synthesis of 4,5-Diaryl-1H-pyrazole-3-ol derivatives as potential COX-2 inhibitors

4,5-Diaryl-1H-pyrazole-3-ol was utilized as a versatile template to synthesize several classes of compounds such as pyrazolo-oxazines 7, pyrazolo-benzooxazines 9, pyrazolo-oxazoles 10, and its analogues 11a-c as potential COX-2 inhibitors. Compounds 11b,c were successfully synthesized with use of pyridinium p-toluenesulfonate mediated cyclization of the ketal intermediate. Diarylpyrazolo-benzooxazepine analogues were synthesized by using Cu-mediated cyclization of the O-alkylated arylbromide intermediate. Arylsulfonamides were synthesized efficiently on a large scale with 4-[4-(4-fluorophenyl)-5-hydroxy-2H-pyrazol-3-yl]benzenesulfonamide 31 template readily synthesized from commercially available 4-sulfamoyl benzoic acid 29. The structure of a representative compound from each class was confirmed by X-ray crystallography. Selected compounds tested for inhibitory activity against COX-1 and COX-2 enzymes showed good selectivity for COX-2 versus COX-1 enzyme.

SULFONYLPHENYLPYRAZOLE COMPOUNDS USEFUL AS COX-2 INHIBITORS

The present invention encompasses novel sulfonylphenylpyrazole compounds useful in the treatment of cyclooxygenase-2 mediated diseases.