1400633-25-1

Basic information

• Product Name: 4-(3-(tert-butyl)-5-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)benzoic acid
• CAS NO: 1400633-25-1
• Molecular Weight: 338.406
• Mol File: 1400633-25-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 4-(3-(tert-butyl)-5-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)benzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(3-(tert-butyl)-5-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)benzoic acid(1400633-25-1)
• EPA Substance Registry System: 4-(3-(tert-butyl)-5-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)benzoic acid(1400633-25-1)

Safety Data

• Hazardous Substances Data: 1400633-25-1(Hazardous Substances Data)

Upstream product

• 75-97-8 3,3-dimethyl-butan-2-one 
• 123-08-0 4-hydroxy-benzaldehyde 
• 24589-77-3 4-hydrazinobenzoic acid hydrochloride 
• 57699-45-3 p-tert-butoxybenzaldehyde 

Relevant articles and documents

Discovery of trisubstituted pyrazolines as a novel scaffold for the development of selective phosphodiesterase 5 inhibitors

Celecoxib, is a selective cyclooxygenase-2 (COX2) inhibitor with a 1,5-diaryl pyrazole scaffold. Celecoxib has a better safety profile compared to other COX2 inhibitors having side effects of systemic hypertension and thromboembolic complications. This may be partly attributed to an off-target activity involving phosphodiesterase 5 (PDE5) inhibition and the potentiation of NO/cGMP signalling allowing coronary vasodilation and aortic relaxation. Inspired by the structure of celecoxib, we synthesized a chemically diverse series of compounds containing a 1,3,5-trisubstituted pyrazoline scaffold to improve PDE5 inhibitory potency, while eliminating COX2 inhibitory activity. SAR studies for PDE5 inhibition revealed an essential role for a carboxylic acid functionality at the 1-phenyl and the importance of the non-planar pyrazoline core over the planar pyrazole with the 5-phenyl moiety tolerating a range of substituents. These modifications led to new PDE5 inhibitors with approximately 20-fold improved potency to inhibit PDE5 and no COX-2 inhibitory activity compared with celecoxib. PDE isozyme profiling of compound 11 revealed a favorable selectivity profile. These results suggest that trisubstituted pyrazolines provide a promising scaffold for further chemical optimization to identify novel PDE5 inhibitors with potential for less side effects compared with available PDE5 inhibitors used for the treatment of penile erectile dysfunction and pulmonary hypertension.

Discovery and optimization of 1,3,5-trisubstituted pyrazolines as potent and highly selective allosteric inhibitors of protein kinase C-χ

There is increasing evidence that the atypical protein kinase C, PKCχ, might be a therapeutic target in pulmonary and hepatic inflammatory diseases. However, targeting the highly conserved ATP-binding pocket in the catalytic domain held little promise to