519137-38-3

Basic information

• Product Name: 3-(1,3-DIPHENYL-1H-PYRAZOL-4-YL)-ACRYLIC ACID
• Synonyms: 3-(1,3-DIPHENYL-1H-PYRAZOL-4-YL)-ACRYLIC ACID
• CAS NO: 519137-38-3
• Molecular Formula: C18H14N2O2
• Molecular Weight: 290.32
• Mol File: 519137-38-3.mol

Chemical Properties

• Melting Point: 203-205 °C
• Boiling Point: 517.9±38.0 °C(Predicted)
• Appearance: /
• Density: 1.17±0.1 g/cm3(Predicted)
• PKA: 3.98±0.10(Predicted)
• 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(519137-38-3)
• EPA Substance Registry System: 3-(1,3-DIPHENYL-1H-PYRAZOL-4-YL)-ACRYLIC ACID(519137-38-3)

Safety Data

• Hazardous Substances Data: 519137-38-3(Hazardous Substances Data)

Upstream product

• 141-82-2 malonic acid 
• 21487-45-6 1,3-diphenyl-4-formylpyrazole 
• 583-11-9 N-(1-phenylethylidene)phenylhydrazine 
• 68-12-2 N,N-dimethyl-formamide 
• 98-86-2 acetophenone 
• 100-63-0 phenylhydrazine 
• 108446-65-7 2-((1,3-diphenyl-1H-pyrazol-4-yl)methylene)malonic acid 
• 108446-83-9 2-(1,3-Diphenyl-1H-pyrazol-4-ylmethylene)-malonic acid diethyl ester 

Relevant articles and documents

(E)-1-phenyl 4-alkenyl-1H-pyrazole compound and medical application thereof

The invention discloses (E)-1-phenyl-4-alkenyl-1H-pyrazole compounds and an application thereof, and belongs to the field of medicinal chemistry. The compound can be covalently bound with specific sulfydryl on Hsp90 protein, and is used for treating various diseases mediated by Hsp90, such as cancer or other proliferative diseases.

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.

Targeting malaria and leishmaniasis: Synthesis and pharmacological evaluation of novel pyrazole-1,3,4-oxadiazole hybrids. Part II

In continuance with earlier reported work, an extension has been carried out by the same research group. Mulling over the ongoing condition of resistance to existing antimalarial agents, we had reported synthesis and antimalarial activity of certain pyrazole-1,3,4-oxadiazole hybrid compounds. Bearing previous results in mind, our research group ideated to design and synthesize some more derivatives with varied substitutions of acetophenone and hydrazide. Following this, derivatives 5a–r were synthesized and tested for antimalarial efficacy by schizont maturation inhibition assay. Further, depending on the literature support and results of our previous series, certain potent compounds (5f, 5n and 5r) were subjected to Falcipain-2 inhibitory assay. Results obtained for these particular compounds further strengthened our hypothesis. Here, in this series, compound 5f having unsubstituted acetophenone part and a furan moiety linked to oxadiazole ring emerged as the most potent compound and results were found to be comparable to that of the most potent compound (indole bearing) of previous series. Additionally, depending on the available literature, compounds (5a–r) were tested for their antileishmanial potential. Compounds 5a, 5c and 5r demonstrated dose-dependent killing of the promastigotes. Their IC50 values were found to be 33.3 ± 1.68, 40.1 ± 1.0 and 19.0 ± 1.47 μg/mL respectively. These compounds (5a, 5c and 5r) also had effects on amastigote infectivity with IC50 of 44.2 ± 2.72, 66.8 ± 2.05 and 73.1 ± 1.69 μg/mL respectively. Further target validation was done using molecular docking studies. Acute oral toxicity studies for most active compounds were also performed.

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.

Synthesis of some 2-({(2E)-3-(1,3-substituted diphenyl-1H-pyrazol-4-yl) prop-2-enoyl} amino) benzoic acids as antiinflammatory agents

Vilsmeier-Haack reaction of substituted phenyl hydrazone derivatives (1a-j) afforded 1,3-substituted diphenyl-1H-pyrazole-4-carbaldehydes (2a-j). Compounds (2a-j) on condensation with malonic acid gave (2E)-3-(1,3-substituted diphenyl-1H-pyrazol-4-yl) acrylic acids (3a-j) which on reaction with thionyl chloride afforded acryloyl chlorides. The reaction of acryloyl chlorides with anthranilic acid gave 2-({(2E)-3-(1,3-substituted diphenyl-1H-pyrazol-4-yl) prop-2-enoyl} amino) benzoic acids (4a-j) in good yields. The structures of the newly synthesized compounds have been confirmed on the basis of physical and spectral data. Some of the synthesized compounds have shown significant antiiflammatory actiivty.

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

Synthesis and biological evaluation of some novel 3-(1,3-diphenyl-1H- pyrazol-4-yl) propanoic acids

Vilsmeier-Haack reaction of phenyl hydrazone derivatives (1a-j) afforded 1,3-diphenyl-1 W-pyrazole-4-carbaldehydes (2a-j). Condensation of (2a-j) with malonic acid gave 3-(1,3-diphenyl-1/-/-pyrazol-4-yl) acrylic acids (3a-j. Reduction of (3a-j) gave 3-(1,

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.

Functionally substituted 3-heterylpyrazoles: XI. 3-[3-Aryl(heteryl)pyrazol-4-yl]propenoic and propanoic acids

3-Aryl(heteryl)-4-formylpyrazoles by condensation with malonic acid furnish 3-[3-aryl(heteryl)-pyrazol-4-yl]propenoic acids that in the presence of Raney nickel are reduced by hydrazine hydrate to 3-[3-aryl(heteryl)pyrazol-4-yl]propanoic acids. The succes

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.