1287761-01-6

Usage

Uses

Used in Pharmaceutical Applications:
[(4-(5-phenyl-3-3-[3-(4-trifluoromethylphenyl)ureido]-propyl-pyrazol-1-yl)-benzenesulfonamide)] is used as a PTUPB (Phenyl-Trifluoromethyl-Ureido-Propyl-Benzenesulfonamide), which acts as a dual inhibitor of COX-2 and sEH (soluble Epoxide Hydrolase). As a PTUPB, it has been shown to alleviate bleomycin-induced pulmonary fibrosis in mice by inhibiting cellular senescence, making it a promising candidate for the treatment of fibrosis-related diseases.
Used in Research and Development:
In the field of research and development, [(4-(5-phenyl-3-3-[3-(4-trifluoromethylphenyl)ureido]-propyl-pyrazol-1-yl)-benzenesulfonamide)] can be utilized as a chemical probe to study the mechanisms of COX-2 and sEH inhibition, as well as their roles in various diseases. [(4-(5-phenyl-3-3-[3-(4-trifluoromethylphenyl)ureido]-propyl-pyrazol-1-yl)-benzenesulfonamide)] can also be used to develop new drugs targeting these enzymes, potentially leading to novel therapeutic strategies for a range of conditions.
Used in Chemical Synthesis:
[(4-(5-phenyl-3-3-[3-(4-trifluoromethylphenyl)ureido]-propyl-pyrazol-1-yl)-benzenesulfonamide)] can be employed as a starting material or intermediate in the synthesis of other complex organic compounds. Its unique structure and functional groups make it a valuable building block for the development of new molecules with potential applications in various industries, such as pharmaceuticals, agrochemicals, and materials science.

Upstream product

• 17852-52-7 4-hydrazinobenzene-1-sulfonamide hydrochloride 
• 1287761-15-2 4-[3-(3-azidopropyl)-5-phenyl-pyrazol-1-yl]-benzenesulfonamide 
• 1548-13-6 p-trifluoromethyl-phenylisocyanate 

Relevant academic research and scientific papers

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.