73221-47-3

Basic information

• Product Name: 3-(1,3-DIPHENYL-1H-PYRAZOL-4-YL)-ACRYLIC ACID
• Synonyms: (Z)-3-(1,3-diphenylpyrazol-4-yl)prop-2-enoic acid
• CAS NO: 73221-47-3
• Molecular Formula: C₁₈H₁₄N₂O₂
• Molecular Weight: 0
• Mol File: 73221-47-3.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 517.9°C at 760 mmHg
• Flash Point: 267°C
• Appearance: /
• Density: 1.17g/cm³
• Vapor Pressure: 1.5E-11mmHg at 25°C
• Refractive Index: 1.618
• CAS DataBase Reference: 3-(1,3-DIPHENYL-1H-PYRAZOL-4-YL)-ACRYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(1,3-DIPHENYL-1H-PYRAZOL-4-YL)-ACRYLIC ACID(73221-47-3)
• EPA Substance Registry System: 3-(1,3-DIPHENYL-1H-PYRAZOL-4-YL)-ACRYLIC ACID(73221-47-3)

Safety Data

• Hazardous Substances Data: 73221-47-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C18H14N2O2/c21-17(22)12-11-15-13-20(16-9-5-2-6-10-16)19-18(15)14-7-3-1-4-8-14/h1-13H,(H,21,22)/b12-11+

Upstream product

• 108446-65-7 2-((1,3-diphenyl-1H-pyrazol-4-yl)methylene)malonic acid 
• 141-82-2 malonic acid 
• 21487-45-6 1,3-diphenyl-4-formylpyrazole 
• 583-11-9 N-(1-phenylethylidene)phenylhydrazine 
• 108446-83-9 2-(1,3-Diphenyl-1H-pyrazol-4-ylmethylene)-malonic acid diethyl ester 
• 98-86-2 acetophenone 
• 100-63-0 phenylhydrazine 

Downstream Products

• 108446-77-1 3-(1,3-diphenyl-1H-pyrazol-4-yl)propanoic acid 
• 519137-53-2 3-(1,3-diphenyl-1H-pyrazol-4-yl)-propionyl chloride 

Relevant articles and documents

Synthesis and SAR studies of novel 1,2,4-oxadiazole-sulfonamide based compounds as potential anticancer agents for colorectal cancer therapy

A diverse series of 1,2,4-oxadiazoles based substituted compounds were designed, synthesized and evaluated as anticancer agents targeting carbonic anhydrase IX (CAIX). Initial structure-activity analysis suggested that the thiazole/thiophene-sulfonamide conjugates of 1,2,4-oxadiazoles exhibited potent anticancer activities with low μM potencies. Compound OX12 exhibited antiproliferative activity (IC50 = 11.1 μM) along with appreciable inhibition potential for tumor-associated CAIX (IC50 = 4.23 μM) isoform. Therefore, OX12 was structurally optimized and its SAR oriented derivatives (OX17-27) were synthesized and evaluated. This iteration resulted in compound OX27 with an almost two-fold increase in antiproliferative effect (IC50 = 6.0 μM) comparable to the clinical drug doxorubicin and significantly higher potency against CAIX (IC50 = 0.74 μM). Additionally, OX27 treatment decreases the expression of CAIX, induces apoptosis and ROS production, inhibited colony formation and migration of colon cancer cells. Our studies provide preclinical rational for the further optimization of identified OX27 as a suitable lead for the possible treatment of CRC.

Synthesis of 3-(1, 3-diphenyl-1H-pyrazol-4-yl) propanoic acids using diimide reduction

Pyrazole-1H-4-yl-acrylic acids (3a-j) were prepared from pyrazole-1H-4-carbaldehydes which in turn were prepared by the Vilsmeier-Haack reaction of phenyl hydrazone derivatives (1a-j). The reaction of pyrazole-1H- 4-yl-acrylic acids to 3-(1, 3-diphenyl-1H

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.