36640-40-1

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
3-(4-FLUORO-PHENYL)-1-PHENYL-1H-PYRAZOLE-4-CARBALDEHYDE is used as a research compound for exploring its various biological activities, such as anti-inflammatory, antibacterial, and anticancer properties. The presence of the fluorophenyl group may confer specific pharmacological properties, making it a promising candidate for the development of novel therapeutic agents.
Used in Organic Synthesis:
Due to its carbaldehyde functional group, 3-(4-FLUORO-PHENYL)-1-PHENYL-1H-PYRAZOLE-4-CARBALDEHYDE is used as a versatile intermediate in organic synthesis. It can be employed in the preparation of various chemical compounds and may serve as a building block for the synthesis of more complex molecules with potential applications in different industries.
Used in Chemical Industry:
3-(4-FLUORO-PHENYL)-1-PHENYL-1H-PYRAZOLE-4-CARBALDEHYDE is used as a chemical intermediate for the production of various specialty chemicals, dyes, and pigments. Its unique structure and functional groups make it a valuable component in the development of new materials with specific properties and applications.

InChI:InChI=1/C16H11FN2O/c17-14-8-6-12(7-9-14)16-13(11-20)10-19(18-16)15-4-2-1-3-5-15/h1-11H

Upstream product

• 403-42-9 1-(4-fluorophenyl)ethanone 
• 68-12-2 N,N-dimethyl-formamide 
• 100-63-0 phenylhydrazine 
• 59-88-1 phenylhydrazine hydrochloride 
• 98-86-2 acetophenone 
• 371-14-2 4-fluorophenylhydrazine 
• 399-19-9 1-(4-fluorophenyl)-2-(1-phenylethylidene)hydrazine 
• 54779-81-6 4-methylacetophenone phenylhydrazone 
• 122-00-9 para-methylacetophenone 
• 352-06-7 1-(4-fluorobenzylidene)-2-phenylhydrazine 
• 1994-40-7 1-(1-(4-fluorophenyl)ethylidene)-2-phenylhydrazine 
• 18997-06-3 N,N-Dimethyl-formamide; compound with GENERIC INORGANIC NEUTRAL COMPONENT 

Downstream Products

• 108446-72-6 3-(p-Fluorphenyl)-1-phenyl-pyrazol-4-yl-acrylsaeure 
• 108446-66-8 3-(p-Fluorphenyl)-1-phenyl-pyrazol-4-yl-methylenmalon-saeure 
• 380449-89-8 Benzyl-[1-[3-(4-fluoro-phenyl)-1-phenyl-1H-pyrazol-4-yl]-meth-(E)-ylidene]-amine 
• 373627-27-1 3-(4-fluoro-phenyl)-1-phenyl-1H-pyrazole-4-carbonyl chloride 
• 1264279-83-5 1-(2-hydroxyphenyl)-3-[(1-phenyl-3-(4-fluorophenyl)-4-pyrazolyl)]prop-2-en-1-one 
• 1263379-84-5 2-[3-(4-fluoro-phenyl)-1-phenyl-1H-pyrazol-4-yl]benzothiazole 
• 484049-04-9 DPH 
• 1262764-27-1 (Z)-5-((3-(4-fluorophenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)-3-phenylthiazolidine-2,4-dione 
• 1394018-49-5 2-(4-chlorophenylimino)-5-((3-(4-fluorophenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)thiazolidin-4-one 
• 1329116-49-5 1-(4-fluorophenyl)-4-[3-(4-fluorophenyl)-1-phenyl-1H-pyrazol-4-yl]-3,4,7,8-tetrahydroquinoline-2,5(1H,6H)-dione 
• 1329116-59-7 4-[3-(4-fluorophenyl)-1-phenyl-1H-pyrazol-4-yl]-1-(4-fluorophenyl)-7,7-dimethyl-3,4,7,8-tetrahydroquinoline-2,5(1H,6H)-dione 
• 1416218-97-7 C₂₈H₂₀FN₃O₃S₂ 
• 1431855-43-4 2-(2,4-dimethoxyphenylamino)-5-[3-(4-fluoro-phenyl)-1-phenyl-1H-pyrazol-4-ylmethylene]thiazol-4-one 
• 1333240-94-0 C₂₄H₁₂ClF₃N₂O₂ 

Relevant academic research and scientific papers

Synthesis of lathyrane diterpenoid nitrogen-containing heterocyclic derivatives and evaluation of their anti-inflammatory activities

As our ongoing work on lathyrane diterpenoid derivatization, three series of lathyrane diterpenoid derivatives were designed and synthesized based combination principles, including pyrazole, thiazole and furoxan moieties. Biological evaluation indicated t

Design, synthesis, biological evaluation, and molecular docking studies of some novel N,N-dimethylaminopropoxy-substituted aurones

In continuation of our ongoing research on the discovery of novel and potentially bioactive aurones, we have designed and synthesized some novel N,N-dimethylaminopropoxy-substituted pyrazole-based aurones 10(a-l). These pyrazole-benzofuranone hybrid compounds were characterized by using their IR, 1H-NMR, 13C-NMR, and mass spectrometry data. Compound 10c was used as a model to further explicate the structure of tilted compounds by means of 1H-1H COSY, 1H-13C HMQC, 1H-13C HMBC, 1H-1H TOCSY, 1H-1H NOSEY, DEPT-45°, DEPT-90°, and DEPT-135° NMR spectra. The comparative molecular docking study of N,N-dimethylaminopropoxy-substituted pyrazole-based aurones and standard drugs (Ampicillin and Chloramphenicol) against Bacillus subtilis (PDB: 6tzp) active site was performed to determine the binding interactions, binding energy, and orientation of the molecules at the active site of the target protein. Out of these synthesized compounds, five best analogs (10b, 10f, 10h, 10k, and 10l) of docking results were also evaluated for their in vitro antibacterial potential against Bacillus subtilis to validate the docking results.

Design and synthesis of pyrazole–pyrazoline hybrids as cancer-associated selective COX-2 inhibitors

In continuation of our previous work on cancer and inflammation, 15 novel pyrazole–pyrazoline hybrids (WSPP1–15) were synthesized and fully characterized. The formation of the pyrazoline ring was confirmed by the appearance of three doublets of doublets in 1H nuclear magnetic resonance spectra exhibiting an AMX pattern for three protons (HA, HM, and HX) of the pyrazoline ring. All the synthesized compounds were screened for their in vitro anticancer activity against five cell lines, that is, MCF-7, A549, SiHa, COLO205, and HepG2 cells, using the MTT growth inhibition assay. 5-Fluorouracil was taken as the positive control in the study. It was observed that, among them, WSPP11 was found to be active against A549, SiHa, COLO205, and HepG2 cells, with IC50 values of 4.94, 4.54, 4.86, and 2.09 μM. All the derivatives were also evaluated for their cytotoxicity against HaCaT cells. WSPP11 was also found to be nontoxic against normal cells (cell line HaCaT), with an IC50 value of more than 50 μM. The derivatives were also evaluated for their in vitro anti-inflammatory activity by the protein (egg albumin) denaturation assay and the red blood cell membrane stabilizing assay, using diclofenac sodium and celecoxib as standard. Compounds that showed significant anticancer and anti-inflammatory activities were further studied for COX-2 inhibition. The manifestation of a higher COX-2 selectivity index of WSPP11 as compared with other derivatives and an in vitro anticancer activity against four cell lines further established that compounds that were more selective toward COX-2 also exhibited a better spectrum of activity against various cancer cell lines.

Design and synthesis of novel pyrazole-phenyl semicarbazone derivatives as potential α-glucosidase inhibitor: Kinetics and molecular dynamics simulation study

A series of novel pyrazole-phenyl semicarbazone derivatives were designed, synthesized, and screened for in vitro α-glucosidase inhibitory activity. Given the importance of hydrogen bonding in promoting the α-glucosidase inhibitory activity, pharmacophore modification was established. The docking results rationalized the idea of the design. All newly synthesized compounds exhibited excellent in vitro yeast α-glucosidase inhibition (IC50 values in the range of 65.1–695.0 μM) even much more potent than standard drug acarbose (IC50 = 750.0 μM). Among them, compounds 8o displayed the most potent α-glucosidase inhibitory activity (IC50 = 65.1 ± 0.3 μM). Kinetic study of compound 8o revealed that it inhibited α-glucosidase in a competitive mode (Ki = 87.0 μM). Limited SAR suggested that electronic properties of substitutions have little effect on inhibitory potential of compounds. Cytotoxic studies demonstrated that the active compounds (8o, 8k, 8p, 8l, 8i, and 8a) compounds are also non-cytotoxic. The binding modes of the most potent compounds 8o, 8k, 8p, 8l and 8i was studied through in silico docking studies. Molecular dynamic simulations have been performed in order to explain the dynamic behavior and structural changes of the systems by the calculation of the root mean square deviation (RMSD) and root mean square fluctuation (RMSF).

Design and synthesis of novel quinazolinone-pyrazole derivatives as potential α-glucosidase inhibitors: Structure-activity relationship, molecular modeling and kinetic study

In this study, a new series of quinazolinone-pyrazole hybrids were designed, synthesized and screened for their α-glucosidase inhibitory activity. The results of the in vitro screening indicated that all the molecular hybrids exhibited more inhibitory activity (IC50 values ranging from 60.5 ± 0.3 μM-186.6 ± 20 μM) in comparison to standard acarbose (IC50 = 750.0 ± 10.0 μM). Limited structure–activity relationship suggested that the variation in the inhibitory activities of the compounds affected by different substitutions on phenyl rings of diphenyl pyrazole moiety. The enzyme kinetic studies of the most potent compound 9i revealed that it inhibited α-glucosidase in a competitive mode with a Ki of 56 μM. Molecular docking study was performed to predict the putative binding interaction. As expected, all pharmacophoric moieties used in the initial structure design playing a pivotal role in the interaction with the binding site of the enzyme. In addition, by performing molecular dynamic investigation and MM-GBSA calculation, we investigated the difference in structural perturbation and dynamic behavior that is observed over α-glycosidase in complex with the most active compound and acarbose relative to unbound α-glycosidase enzyme.

H3PO4 catalyzed one-pot synthesis of 1,3-diphenyl-1H-pyrazole-4-carbaldehyde to novel 1,3-diphenyl-1H-pyrazole-4-carbonitrile

Abstract: One-pot condensation of pyrazole-4-aldehydes and hydroxylamine hydrochloride to form the corresponding oxime using formic acid as a medium and further dehydration of oxime using a catalytic amount of orthophosphoric acid to afford novel pyrazole-4-carbonitrile. This protocol serves as an ortho-phosphoric acid-catalyzed one-pot conversion of aldehyde to nitrile. Most remarkable features of this method are metal-free, cost-effective, atom efficiency with excellent yield (98–99%). This process will serve as a robust and scalable tool for the synthesis of valuable and versatile precursor (nitriles). This precursor will pave the way for the synthesis of various medicinally important valuable compounds. Graphic abstract: [Figure not available: see fulltext.].

New library of pyrazole–imidazo[1,2-α]pyridine molecular conjugates: Synthesis, antibacterial activity and molecular docking studies

A library of novel pyrazole–imidazo[1,2-α]pyridine scaffolds was designed and synthesized through a one-pot three-component tandem reaction. The structures of synthesized conjugates were confirmed by spectroscopic techniques (NMR, IR and HRMS). In vitro antibacterial evaluation of the twelve synthesized molecules (7a, 8a–k) against methicillin-resistant Staphylococcus aureus and normal strains of Escherichia coli, Salmonella typhimurium, Klebsiella pneumonia and Pseudomonas aeruginosa established 8b, 8d, 8e, 8h and 8i as potent antibacterial agents with superior minimum bactericidal concentration, compared with standard drug ciprofloxacin. Molecular docking studies of all active compounds into the binding site of glucosamine-6-phosphate synthase were further performed in order to have a comprehensive understanding of putative binding modes within the active sites of the receptor.

Novel pyrazole-clubbed thiophene derivatives via Gewald synthesis as antibacterial and anti-inflammatory agents

The aim of this study was to synthesize newer potent Schiff bases by condensing 2-amino-5-(2,4-dichlorophenyl)thiophene-3-carbonitrile and 1,3-disubstituted-1H-pyrazole-4-carbaldehydes, and to investigate their biological activity. The compounds were synthesized via Gewald synthesis and characterized by spectral data and elemental analyses. They were screened for their in vitro antibacterial and anti-inflammatory activities. The synthesized compounds were also evaluated for in vitro antitubercular activity against Mycobacterium tuberculosis H37Rv using the microplate Alamar Blue assay. Compounds 8b, 8c, 8f, 8g, 8k, 8n, and 8o showed promising antibacterial activity. The interactions between the substituted pyrazoles and bovine protein showed promising anti-inflammatory activity. The experimental results revealed compound 8a as a promising antitubercular agent. Hemolytic assays confirmed that the compounds are nontoxic, with percentage hemolysis ranging from 3.6 to 20.1, at a concentration of 1 mg/ml. The results suggest that the pyrazole ring and the substitution pattern on the heterocyclic moiety have an effect on the bioactivity.

Microwave-Assisted Synthesis and Antimicrobial Activity of Novel Pyrazole–Indanone Hybrid Analogs

Abstract: A simple and efficient microwave-assisted protocol has been developed for the synthetic of a series of novel pyrazole–indanone hybrid analogs. The target compounds have been synthesized by the Claisen–Schmidt condensation of different 1,3-diphenyl-1H-pyrazole-4-carbaldehydes with 2,3-dihydro-1H-inden-1-one in the presence of potassium hydroxide. The compounds were characterized by IR, 1H and 13C NMR, and mass spectra and were found to exhibit potent antimicrobial activity in vitro.

Pyrazolylphenanthroimidazole heterocycles: Synthesis, biological and molecular docking studies

The synthesis of a series of novel pyrazolylphenanthroimidazoles 6a-6j has been accomplished utilizing a multi-step synthetic protocol, and characterized through physical and spectral techniques. Among them, the molecules possessing para-bromo (6d), para-methyl (6f) and para-nitro (6j) phenyl substituents on the pyrazole scaffold displayed similar anti-inflammatory activity and the one with no substituents on the aryl unit (6a) exhibited the highest anti-inflammatory profile. While investigating the DPPH radical scavenging activity, the synthesized chemical entity with a para-methoxyphenyl group attached at the pyrazole structural motif (6i) revealed the highest activity when compared to the other synthesized molecules. Furthermore, the evaluation of cytotoxic activity of the synthesized molecule (6a) exerted significant activity against both the pancreatic cell lines such as AsPC1 and SW1990. Besides, while performing the molecular docking studies of 6a with B-cell lymphoma 2, an appreciable binding affinity (-9.04 kcal mol-1) has been observed. The results of the present examination imply that these chemical entities could be used as efficient intermediates for the construction of biopertinent molecules. This journal is