781663-70-5

Upstream product

• 88330-79-4 ethyl-(Z)-2-hydroxy-4-oxo-4-phenyl-but-2-enoate 
• 4392-54-5 4-aminosulfonylphenylhydrazine 
• 98-86-2 acetophenone 
• 17852-52-7 4-hydrazinobenzene-1-sulfonamide hydrochloride 
• 88330-79-4 2-hydroxy-4-oxo-4-phenylbut-2-enoic acid ethyl ester 
• 3453-00-7 diethyl benzoylmethylphosphonate 
• 96722-53-1 C₁₀H₁₂ClN₃O₄S 
• 6296-54-4 ethyl 2,4-dioxo-4-phenylbutyrate 
• 63-74-1 sulfanilamide 

Downstream Products

• 170570-84-0 4-[3-hydroxymethyl-5-phenyl-1H-pyrazol-1-yl]benzene Sulfonamide 
• 781663-80-7 1-(4-aminosulfonylphenyl)-3-bromomethyl-5-phenyl-1H-pyrazole 
• 1287760-83-1 4-{5-phenyl-3-[3-(3-trifluoromethylphenyl)-ureido]-pyrazol-1-yl}-benzenesulfonamide 
• 1287761-04-9 4-(3-azidomethyl-5-phenyl-pyrazol-1-yl)-benzenesulfonamide 
• 1287760-90-0 4-{5-phenyl-3-[3-(3-trifluoromethylphenyl)-ureidomethyl]-pyrazol-1-yl}-benzenesulfonamide 
• 1287761-13-0 4-[3-((E)-2-nitro-vinyl)-5-phenyl-pyrazol-1-yl]-benzenesulfonamide 
• 1287761-14-1 4-[3-(2-aminoethyl)-5-phenyl-pyrazol-1-yl]-benzenesulfonamide 
• 1287760-92-2 4-(5-phenyl-3-{2-[3-(3-trifluoromethylphenyl)-ureido]-ethyl}-pyrazol-1-yl)-benzenesulfonamide 
• 1287760-82-0 [5-phenyl-1-(4-sulfamoylphenyl)-1H-pyrazol-3-yl]-carbamic acid ethyl ester 
• 476322-49-3 4-(3-amino-5-phenyl-pyrazol-1-yl)-benzenesulfonamide 
• 586333-65-5 5-phenyl-1-(4-sulfamoylphenyl)-1H-pyrazole-3-carboxylic acid 

Relevant academic research and scientific papers

Discovery of novel urea-diarylpyrazole hybrids as dual COX-2/sEH inhibitors with improved anti-inflammatory activity and highly reduced cardiovascular risks

Herein we describe our efforts to develop novel anti-inflammatory/analgesic agents devoid of known cardiovascular drawbacks. In doing so, two 1,5-diarylpyrazole series of urea linked (9a-f) and amide linked (11a-f) compounds were synthesized and evaluated

Synthesis, biological evaluation and in silico modelling studies of 1,3,5-trisubstituted pyrazoles carrying benzenesulfonamide as potential anticancer agents and selective cancer-associated hCA IX isoenzyme inhibitors

Inhibition of carbonic anhydrases (CAs, EC 4.2.1.1) has clinical importance for the treatment of several diseases. They participate in crucial regulatory mechanisms for balancing intracellular and extracellular pH of the cells. Among CA isoforms, selectiv

Anti-inflammatory Exploration of Sulfonamide Containing Diaryl Pyrazoles with Promising COX-2 Selectivity and Enhanced Gastric Safety Profile

Novel sulfonamide containing diaryl pyrazoles were synthesized and were subsequently tested for their in vitro cyclooxygenase inhibitory assay. Compounds that showed promising in vitro COX-2 IC50 values and selectivity indices were then evaluat

LOCALLY BIOAVAILABLE DRUGS

Drugs have been designed and developed with a structural motif allowing local bioavailability in the target organ but that are not broadly distributed at a concentration sufficient to illicit toxic side effects in non-targeted organs. The structural motif

Isatin-pyrazole benzenesulfonamide hybrids potently inhibit tumor-associated carbonic anhydrase isoforms IX and XII

New series of benzenesulfonamide derivatives incorporating pyrazole and isatin moieties were prepared using celecoxib as lead molecule. Biological evaluation of the target compounds was performed against the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1) and more precisely against the human isoforms hCA I, II (cytosolic), IX and XII (transmembrane, tumor-associated enzymes). Most of the tested compounds efficiently inhibited hCA I, II and IX, with KIs of 2.5-102 nM, being more effective than the reference drug acetazolamide. Compounds 11e, 11f, 16e and 16f were found to inhibit hCA XII with Ki of 3.7, 6.5, 5.4 and 7.2 nM, respectively. Compounds 11e and 16e, with 5-NO2substitution on the isatin ring, were found to be selective inhibitors of hCA IX and hCA XII. Docking studies revealed that the NO2group of both compounds participate in interactions with Asp132 within the hCA IX active site, and with residues Lys67 and Asp130 in hCA XII, respectively.

A new efficient synthesis of pyrazoles from hydrazonoyl halides and β-oxophosphonates

A new practical and efficient synthesis of 1,3,5-trisubstituted pyrazoles has been developed by reacting of hydrazonoyl halides with β-oxophosphonates under mild conditions in good yields with excellent regioselectivity. This process employs an addition-elimination sequence. Wide scope, functional group compatibility has been established.

A new efficient synthesis of pyrazoles from hydrazonoyl halides and β-oxophosphonates

A new practical and efficient synthesis of 1,3,5-trisubstituted pyrazoles has been developed by reacting of hydrazonoyl halides with β- oxophosphonates under mild conditions in good yields with excellent regioselectivity. This process employs an addition-elimination sequence. Wide scope, functional group compatibility has been established.

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.

New selective carbonic anhydrase IX inhibitors: Synthesis and pharmacological evaluation of diarylpyrazole-benzenesulfonamides

Carbonic anhydrase (CA) IX expression is increased upon hypoxia and has been proposed as a therapeutic target since it has been associated with poor prognosis, tumor progression and pH regulation. We report the synthesis and the pharmacological evaluation

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.