108446-74-8

Basic information

• Product Name: 3-(1-PHENYL-3-P-TOLYL-1H-PYRAZOL-4-YL)-ACRYLIC ACID
• Synonyms: 3-(1-Phenyl-3-p-tolyl-1H-pyrazol-4-yl)-acrylic acid; (2E)-3-[3-(4-methylphenyl)-1-phenyl-1H-pyrazol-4-yl]prop-2-enoic acid; (2E)-3-[3-(4-methylphenyl)-1-phenyl-1H-pyrazol-4-yl]prop-2-enoate
• CAS NO: 108446-74-8
• Molecular Formula: C₁₉H₁₆N₂O₂
• Molecular Weight: 303.34
• Mol File: 108446-74-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 523.7 °C at 760 mmHg
• Flash Point: 270.5 °C
• Appearance: /
• Vapor Pressure: 8.55E-12mmHg at 25°C
• CAS DataBase Reference: 3-(1-PHENYL-3-P-TOLYL-1H-PYRAZOL-4-YL)-ACRYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(1-PHENYL-3-P-TOLYL-1H-PYRAZOL-4-YL)-ACRYLIC ACID(108446-74-8)
• EPA Substance Registry System: 3-(1-PHENYL-3-P-TOLYL-1H-PYRAZOL-4-YL)-ACRYLIC ACID(108446-74-8)

Safety Data

• Hazardous Substances Data: 108446-74-8(Hazardous Substances Data)

Usage

General Description

3-(1-phenyl-3-p-tolyl-1H-pyrazol-4-yl)-acrylic acid is a chemical compound containing a pyrazole ring and an acrylic acid moiety. It is commonly used in organic synthesis and medicinal chemistry as a building block for the preparation of various pharmaceuticals and bioactive molecules. The compound is known for its potential anti-inflammatory and anti-cancer properties and has also been studied for its role in the treatment of diseases such as diabetes and Alzheimer's. Its unique structure and functional groups make it a versatile and valuable compound for the development of new drugs and therapeutic agents. However, further research and clinical studies are required to fully understand and harness the potential of 3-(1-phenyl-3-p-tolyl-1H-pyrazol-4-yl)-acrylic acid in the field of medicine and pharmacology.

InChI:InChI=1/C19H16N2O2/c1-14-7-9-15(10-8-14)19-16(11-12-18(22)23)13-21(20-19)17-5-3-2-4-6-17/h2-13H,1H3,(H,22,23)/p-1/b12-11+

Upstream product

• 108446-69-1 2-(1-Phenyl-3-p-tolyl-1H-pyrazol-4-ylmethylene)-malonic acid 
• 141-82-2 malonic acid 
• 36640-52-5 1-phenyl-3-(p-tolyl)-1H-pyrazole-4-carbaldehyde 
• 108446-87-3 2-(1-Phenyl-3-p-tolyl-1H-pyrazol-4-ylmethylene)-malonic acid diethyl ester 
• 54779-81-6 4-methylacetophenone phenylhydrazone 
• 59-88-1 phenylhydrazine hydrochloride 
• 122-00-9 para-methylacetophenone 
• 100-63-0 phenylhydrazine 

Downstream Products

• 108446-81-7 3-(1-Phenyl-3-p-tolyl-1H-pyrazol-4-yl)-propionic acid 
• 519137-55-4 3-(1-phenyl-3-p-tolyl-1H-pyrazol-4-yl)-propionyl chloride 
• 1007543-23-8 N-(4-chlorophenyl)-3-(1-phenyl-3-(p-tolyl)-1H-pyrazol-4-yl)acrylamide 
• 380463-49-0 (4-methoxyphenyl)-3-(1-phenyl-3-(p-tolyl)-1H-pyrazol-4-yl)acrylamide 
• 380463-48-9 N-phenyl-3-(1-phenyl-3-(p-tolyl)-1H-pyrazol-4-yl)acrylamide 
• 1390681-83-0 N-(4-bromophenyl)-3-(1-phenyl-3-(p-tolyl)-1H-pyrazol-4-yl)acrylamide 

Relevant articles and documents

Unveiling novel diphenyl-1H-pyrazole based acrylates tethered to 1,2,3-triazole as promising apoptosis inducing cytotoxic and anti-inflammatory agents

Meagre and suboptimal therapeutic response along with the side effect profile associated with the existing anticancer therapy have necessitated the development of new therapeutic modalities to curb this disease. Bearing in mind the current scenario, a series of 1,2,3-triazole linked 3-(1,3-diphenyl-1H-pyrazol-4-yl)acrylates was synthesized following a multi-step reaction scheme. Initial screening for anticancer potential was done by in vitro sulforhodamine B assay against four human cancer cell lines- MCF-7 (breast), A549 (Lung) and HCT-116 and HT-29 (Colon). On evaluation, several compounds showed promising growth inhibition against all the cell lines, particularly compounds 6e, 6f and 6n. Among them, compound 6f displayed IC50 values of 1.962, 3.597, 1.764 and 4.496 μM against A549, HCT-116, MCF-7 and HT-29 cell lines respectively. Furthermore, the apoptosis inducing potential of the compounds was determined by Hoechst staining and DNA fragmentation assay. Colony formation inhibition assay was also carried out to determine the long term cytotoxic potential of the molecules. Moreover, compounds 6e, 6f and 6n were also evaluated for anti-inflammatory activity by protein albumin denaturation assay and red blood cell membrane stabilizing assay.

Microwave-Assisted Synthesis of 3-(4-Pyrazolyl)propenoic Acids

Under microwave activation, pyrazole-4-carboxaldehydes react with malonic acid in the presence of a small amount of pyridine to give 3-(4-pyrazolyl)propenoic acids in high yields.

Azoles. 17. Beta-(4-pyrazol)acrylic and propionic acids and their anti-inflammatory activity

beta-(4-Pyrazole)acrylic acids 22-28 were prepared by the Knoevenagel reaction of malonic acid and 4-formylpyrazoles 8-14. 4-Pyrazolemethylenemalonic acids 15-21 were isolated as intermediates. The latter compounds were also synthesized by treating the 4-formylpyrazoles 8-14 with diethyl malonate followed by hydrolysis of the obtained diethyl esters 15a-21a. The effect of piperidine and pyridine on the Knoevenagel condensation was investigated. The beta-(4-pyrazole)acrylic acids 22-27, on catalytic reduction, gave the corresponding beta-(4-pyrazole)propionic acids 29-34. Compounds 23, 24, 27, 29-31 and 34 appeared to be less active than phenylbutazone in carrageenin-induced oedema test, but they were less toxic than the reference drug.