443919-99-1

Basic information

• Product Name: 1H-Pyrazole-3-carboxylic acid, 1-[4-(methylsulfonyl)phenyl]-5-phenyl-, ethyl ester
• CAS NO: 443919-99-1
• Molecular Formula: C19H18N2O4S
• Molecular Weight: 370.429
• Mol File: 443919-99-1.mol

Chemical Properties

• CAS DataBase Reference: 1H-Pyrazole-3-carboxylic acid, 1-[4-(methylsulfonyl)phenyl]-5-phenyl-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrazole-3-carboxylic acid, 1-[4-(methylsulfonyl)phenyl]-5-phenyl-, ethyl ester(443919-99-1)
• EPA Substance Registry System: 1H-Pyrazole-3-carboxylic acid, 1-[4-(methylsulfonyl)phenyl]-5-phenyl-, ethyl ester(443919-99-1)

Safety Data

• Hazardous Substances Data: 443919-99-1(Hazardous Substances Data)

Upstream product

• 17852-67-4 4-(methylsulfonyl)phenylhydrazine hydrochloride 
• 98-86-2 acetophenone 
• 88330-79-4 ethyl-(Z)-2-hydroxy-4-oxo-4-phenyl-but-2-enoate 
• 6296-54-4 ethyl 2,4-dioxo-4-phenylbutyrate 

Downstream Products

• 1287761-03-8 3-azidomethyl-1-(4-methanesulfonylphenyl)-5-phenyl-1H-pyrazole 
• 1287761-05-0 C-[1-(4-methanesulfonylphenyl)-5-phenyl-1H-pyrazol-3-yl]methylamine 
• 1287760-84-2 1-adamantan-1-yl-3-[1-(4-methanesulfonyl-phenyl)-5-phenyl-1H-pyrazol-3-ylmethyl]-urea 
• 1287760-85-3 1-cycloheptyl-3-[1-(4-methanesulfonylphenyl)-5-phenyl-1H-pyrazol-3-ylmethyl]-urea 
• 1287760-86-4 1-[1-(4-methanesulfonyl-phenyl)-5-phenyl-1H-pyrazol-3-ylmethyl]-3-phenyl-urea 
• 1287760-87-5 1-[1-(4-methanesulfonylphenyl)-5-phenyl-1H-pyrazol-3-ylmethyl]-3-(4-trifluoromethoxyphenyl)-urea 
• 1287760-88-6 1-[1-(4-methanesulfonylphenyl)-5-phenyl-1H-pyrazol-3-ylmethyl]-3-(4-trifluoromethylphenyl)-urea 
• 1287760-89-7 1-[1-(4-methanesulfonylphenyl)-5-phenyl-1H-pyrazol-3-ylmethyl]-3-(3-trifluoromethylphenyl)-urea 
• 1287761-07-2 1-(4-methanesulfonylphenyl)-5-phenyl-1H-pyrazole-3-carbaldehyde 
• 1287761-08-3 (E)-3-[1-(4-methanesulfonylphenyl)-5-phenyl-1H-pyrazol-3-yl]-acrylic acid ethyl ester 
• 1287761-09-4 3-[1-(4-methanesulfonylphenyl)-5-phenyl-1H-pyrazol-3-yl]-propionic acid ethyl ester 
• 1287761-10-7 3-[1-(4-methanesulfonylphenyl)-5-phenyl-1H-pyrazol-3-yl]-propan-1-ol 
• 1287761-11-8 2-{3-[1-(4-methanesulfonylphenyl)-5-phenyl-1H-pyrazol-3-yl]-propyl}-isoindole-1,3-dione 
• 1287761-12-9 C₁₉H₂₁N₃O₂S 

Relevant articles and documents

PYRAZOLE INHIBITORS OF COX-2 AND SEH

The present invention provides compounds and compositions, e.g., a series of compounds wherein a 1,5-biarylpyrazole group is conjugated to a urea group by a non-cleavable covalent chain, that are useful as dual COX-2/sEH inhibitors. The compounds disclosed herein have activity associated with the arachidonate cascade. The activity of these compounds was demonstrated using a lipopolysaccharide (LPS) induced model of pain in the rat. The compounds of the present invention demonstrated superior anti-allodynic activity as compared to the same dose of celecoxib, i.e., a COX-2 inhibitor, also as compared to the same dose of t-AUCB, i.e., a sEH inhibitor, and also as compared to the co-administered same dose of both celecoxib and t-AUCB. The dual inhibitors of the present invention demonstrate enhanced in vivo anti-allodynic activity in a nociceptive behavioral assay. In addition, the compounds of the present invention also demonstrated to have potent anti-angiogenic effects toward endothelial cells (HUVEC) and inhibit angiogenesis in vitro, ex vivo and in vivo. The dual inhibitors of the present invention also demonstrate anti-angiogenic effect to slow breast tumor growth in vivo.

Synthesis and structure-activity relationship studies of urea-containing pyrazoles as dual inhibitors of cyclooxygenase-2 and soluble epoxide hydrolase

A series of dual inhibitors containing a 1,5-diarylpyrazole and a urea were designed, synthesized, and evaluated as novel COX-2/sEH dual inhibitors in vitro using recombinant enzyme assays and in vivo using a lipopolysaccharide (LPS) induced model of pain in rats. The best inhibition potencies and selectivity for sEH and COX-2 over COX-1 were obtained with compounds (21b, 21i, and 21j) in which both the 1,5-diaryl-pyrazole group and the urea group are linked with a three-methylene group. Compound 21i showed the best pharmacokinetic profiles in both mice and rats (higher AUC and longer half-life). Following subcutaneous administration at 10 mg/kg, compound 21i exhibited antiallodynic activity that is more effective than the same dose of either a COX-2 inhibitor (celecoxib) or a sEH inhibitor (t-AUCB) alone, as well as coadministration of both inhibitors. Thus, these novel dual inhibitors exhibited enhanced in vivo antiallodynic activity in a nociceptive behavioral assay.

New COX-2/5-LOX inhibitors: Apoptosis-inducing agents potentially useful in prostate cancer chemotherapy

The arachidonic acid metabolizing enzymes cyclooxygenase-2 (COX-2) and lipoxygenases (LOXs) have been found to be implicated in a variety of cancers, including prostate cancer. To develop new therapeutic treatments, it therefore seemed interesting to design dual COX-2/5-LOX inhibitors. We report here the synthesis and in vitro pharmacological properties of diarylpyrazole derivatives that have in their structure key pharmacophoric elements to obtain optimal interaction with subsites of active pockets in both enzyme systems. Using a molecular modeling approach, a set of SAR data is proposed, highlighting the importance of the sulfonyl group of one of the aryl moieties in terms of proliferation inhibition and/or apoptosis induction.

Synthesis and activity of a new methoxytetrahydropyran derivative as dual cyclooxygenase-2/5-lipoxygenase inhibitor

Dual COX-2/5-LO inhibitors are described as potential new therapeutic agents for inflammatory diseases. A surprisingly potent effect of a 5-LO pharmacophoric group on the COX-2 inhibition is presented as well as pharmacological in vitro and in vivo results.