67962-20-3

Basic information

• Product Name: C₁₃H₁₅BrO
• Synonyms: C₁₃H₁₅BrO
• CAS NO: 67962-20-3
• Molecular Weight: 267.166
• Mol File: 67962-20-3.mol

Chemical Properties

• CAS DataBase Reference: C₁₃H₁₅BrO(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₃H₁₅BrO(67962-20-3)
• EPA Substance Registry System: C₁₃H₁₅BrO(67962-20-3)

Safety Data

• Hazardous Substances Data: 67962-20-3(Hazardous Substances Data)

Upstream product

• 75-97-8 3,3-dimethyl-butan-2-one 
• 6630-33-7 ortho-bromobenzaldehyde 
• 814-16-4 diethyl (3,3-dimethyl-2-oxobutyl)phosphonate 

Downstream Products

• 167367-66-0 (E)-1-bromo-2-(3'-hydroxy-4',4'-dimethylpent-1'-enyl)benzene 
• 1400633-32-0 4-(5-(2-bromophenyl)-3-(tert-butyl)-4,5-dihydro-1H-pyrazol-1-yl)benzoic acid 
• 167368-02-7 C₂₈H₄₂N₂O₃SSi 
• 167368-12-9 Benzoic acid (E)-1-tert-butyl-3-[2-(1-diazo-ethyl)-phenyl]-allyl ester 
• 167368-05-0 C₂₂H₂₈N₂O₃S 
• 167367-92-2 (E)-1-(2'-acetylphenyl)-4,4-dimethylpent-1-en-3-yl benzoate 
• 167367-91-1 (E)-1-<2'(3-tert-butyldimethylsiloxy-4,4-dimethylpent-1-enyl)phenyl>ethanone 
• 167367-79-5 2-[(E)-3-(tert-Butyl-dimethyl-silanyloxy)-4,4-dimethyl-pent-1-enyl]-benzaldehyde 
• 167367-73-9 (E)-1-bromo-2<3'-(tert-butyldimethylsiloxy)-4',4'-dimethylpent-1'-enyl>benzene 
• 167367-93-3 (E)-1-<2'-(3-hydroxy-4,4-dimethylpent-1-enyl)phenyl>ethanone 
• 167367-72-8 (E)-1-bromo-2-(3'-methoxy-4',4'-dimethylpent-1'-enyl)benzene 
• 167368-11-8 tert-Butyl-{(E)-1-tert-butyl-3-[2-(1-diazo-ethyl)-phenyl]-allyloxy}-dimethyl-silane 

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.

Asymmetric Induction in the Electrocyclisations of 1,3 Dipolar Intermediates: the 1.7 Cyclisation of Diene-conjugated Diazo-compounds to give 1H-2,3-Benzodiazepines

In the cyclisation of the diene-conjugated diazo compounds 4 to give the diastereomeric pair of 1H-2,3-benzodiazepines 7 and 8, alkyl and silyl ethers when present as the 'medium' sized group R3, showed the opposite effect in controlling face selectivity