179055-93-7

Basic information

• Product Name: 3-(1-METHYL-1H-PYRAZOL-4-YL)BENZALDEHYDE
• Synonyms: 3-(1-METHYL-1H-PYRAZOL-4-YL)BENZALDEHYDE
• CAS NO: 179055-93-7
• Molecular Formula: C₁₁H₁₀N₂O
• Molecular Weight: 186.2099
• Mol File: 179055-93-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-(1-METHYL-1H-PYRAZOL-4-YL)BENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(1-METHYL-1H-PYRAZOL-4-YL)BENZALDEHYDE(179055-93-7)
• EPA Substance Registry System: 3-(1-METHYL-1H-PYRAZOL-4-YL)BENZALDEHYDE(179055-93-7)

Safety Data

• Hazardous Substances Data: 179055-93-7(Hazardous Substances Data)

Upstream product

• 3132-99-8 m-bromobenzoic aldehyde 
• 847818-55-7 (1-methyl-1H-pyrazol-4-yl)boronic acid 
• 930-36-9 1-methyl-1H-pyrazole 
• 179055-21-1 1-methyl-4-tributylstannanyl-1H-pyrazole 

Downstream Products

• 179056-73-6 Benzyl-[3-(1-methyl-1H-pyrazol-4-yl)-benzyl]-amine 
• 179056-39-4 Cycloheptyl-[3-(1-methyl-1H-pyrazol-4-yl)-benzyl]-amine 

Relevant articles and documents

Probing the Azaaurone Scaffold against the Hepatic and Erythrocytic Stages of Malaria Parasites

The potential of azaaurones as dual-stage antimalarial agents was investigated by assessing the effect of a small library of azaaurones on the inhibition of liver and intraerythrocytic lifecycle stages of the malaria parasite. The whole series was screened against the blood stage of a chloroquine-resistant Plasmodium falciparum strain and the liver stage of P. berghei, yielding compounds with dual-stage activity and sub-micromolar potency against erythrocytic parasites. Studies with genetically modified parasites, using a phenotypic assay based on the P. falciparum Dd2-ScDHODH line, which expresses yeast dihydroorotate dehydrogenase (DHODH), showed that one of the azaaurone derivatives has the potential to inhibit the parasite mitochondrial electron-transport chain. The global urgency in finding new therapies for malaria, especially against the underexplored liver stage, associated with chemical tractability of azaaurones, warrants further development of this chemotype. Overall, these results emphasize the azaaurone chemotype as a promising scaffold for dual-stage antimalarials.

Pd-catalysed direct 5-arylation of 1-methylpyrazole with aryl bromides

1-Methylpyrazole was found to be a suitable partner for palladium-catalysed direct arylation through C-H activation/functionalisation using aryl bromides. The reaction conditions and the nature of the catalyst were found to have a determining influence on

Inhibitors of acyl-coA:cholesterol O-acyltransferase. 2. Identification and structure-activity relationships of a novel series of N-alkyl-N- (heteroaryl-substituted benzyl)-N'-arylureas

A series of N-alkyl-N-(heteroaryl-substituted benzyl)-N'-arylurea and related derivatives represented by 2 and 3 have been prepared and evaluated for their ability to inhibit acyl-CoA:cholesterol O-acyltransferase in vitro and to lower plasma cholesterol levels in cholesterol-fed rats in vivo. Among these novel compounds, the type 3 series was superior. A pyrazol-3-yl group on the N-benzyl group of this trisubstituted urea (i.e. 3, Ar1 = pyrazol-3- yl) was identified as a heteroaromatic ring providing a good profile of biological activity. As a result of optimization of the combination with the N-alkyl group (R) and N-aryl group (At3), compound 3aq (FR186054) was identified as a new, orally efficacious ACAT inhibitor, which exhibited potent in vitro ACAT inhibitory activity (rabbit intestinal microsomes IC50 = 99 nM) and excellent hypocholesterolemic effects in cholesterol-fed rats, irrespective of administration mode (ED50 = 0.046 mg/kg dosed via the diet, ED50 = 0.44 mg/kg administered by gavage in PEG400 vehicle). Moreover, a toxicological study revealed compound 3aq to be nontoxic to the adrenal glands of dogs when tested at a single dose of 10 mg/kg po.