21487-49-0

Usage

Uses

Used in Pharmaceutical Development:
3-(4-NITRO-PHENYL)-1-PHENYL-1H-PYRAZOLE-4-CARBALDEHYDE is used as a building block for the development of pharmaceuticals due to its potential to form biologically active compounds, contributing to the advancement of new drug discoveries.
Used in Agrochemical Development:
In the agrochemical industry, 3-(4-NITRO-PHENYL)-1-PHENYL-1H-PYRAZOLE-4-CARBALDEHYDE is used as a precursor for the synthesis of agrochemicals, playing a crucial role in the development of new pesticides and other agricultural chemicals.
Used in Cancer Research:
3-(4-NITRO-PHENYL)-1-PHENYL-1H-PYRAZOLE-4-CARBALDEHYDE is used as a fluorescent probe for the detection of nitroreductase in tumor cells, aiding researchers in understanding the behavior of cancer cells and potentially contributing to the development of targeted cancer therapies.

InChI:InChI=1/C16H11N3O3/c20-11-13-10-18(14-4-2-1-3-5-14)17-16(13)12-6-8-15(9-7-12)19(21)22/h1-11H

Upstream product

• 68-12-2 N,N-dimethyl-formamide 
• 77635-72-4 1-(4-nitro-phenyl)-ethanone-phenylhydrazone 
• 100-63-0 phenylhydrazine 
• 100-19-6 (4-nitrophenyl)ethanone 
• 77635-72-4 (E)?1-(1-(4-nitrophenyl)ethylidene)-2-phenylhydrazine 
• 20147-63-1 3-(4-nitrophenyl)-1-phenyl-1H-pyrazole 
• 98-86-2 acetophenone 
• 100-16-3 4-nitrophenylhydrazone 
• 59-88-1 phenylhydrazine hydrochloride 
• 2675-22-1 acetophenone p-nitrophenylhydrazone 

Downstream Products

• 1129458-46-3 C₂₈H₂₈N₆O₉S 
• 21487-50-3 1-phenyl-3-(4-nitrophenyl)-1H-pyrazole-4-carboxaldehyde semicarbazone 
• 952648-01-0 C₂₄H₁₇N₃O₄ 
• 1017505-71-3 N-benzoyl-N'-[1-phenyl-3-(4-nitrophenyl)-4-pyrazolylidene]hydrazine 
• 1017500-94-5 C₂₃H₁₆N₆O₅ 
• 1188421-76-2 C₂₃H₁₆ClN₅O₃ 
• 1256486-45-9 C₂₂H₁₄N₄O₂S 
• 1255792-93-8 ethyl 4-(3-(4-nitrophenyl)-1-phenyl-1H-pyrazol-4-yl)-1,2,3,4-tetrahydro-2-imino-6-methylpyrimidine-5-carboxylate 
• 1255792-89-2 ethyl 4-(3-(4-nitrophenyl)-1-phenyl-1H-pyrazol-4-yl)-1,2,3,4-tetrahydro-6-methyl-2-thioxopyrimidine-5-carboxylate 
• 1255792-88-1 ethyl 4-(3-(4-nitrophenyl)-1-phenyl-1H-pyrazol-4-yl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 
• 1255792-95-0 methyl 6-methyl-4-(3-(4-nitrophenyl)-1-phenyl-1H-pyrazol-4-yl)-2-thio-1,2,3,4-tetrahydropyrimidine-5-carboxylate 
• 1255792-96-1 methyl 4-(3-(4-nitrophenyl)-1-phenyl-1H-pyrazol-4-yl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 
• 1276543-09-9 2-amino-1-(4-(4-fluorophenyl)thiazol-2-yl)-4-(3-(4-nitrophenyl)-1-phenyl-1H-pyrazol-4-yl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile 
• 1276543-18-0 2-amino-1-(4-(4-fluorophenyl)thiazol-2-yl)-7,7-dimethyl-4-(3-(4-nitrophenyl)-1-phenyl-1H-pyrazol-4-yl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile 

Relevant academic research and scientific papers

1,3,4-Trisubstituted pyrazole analogues as promising anti-inflammatory agents

Twenty-two 1,3,4-trisubstituted pyrazole (3a-d), (4a-d), (5a-d), (6a-l) derivatives were synthesized and structure of newly synthesized compounds were characterized by IR, 1H NMR, 13C NMR, and mass spectral analysis. These compounds

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.

Synthesis, biological evaluation, and molecular docking studies of novel pyrazole, pyrazoline-clubbed pyridine as potential antimicrobial agents

We have prepared 15 hybrid pyrazole, pyrazoline-clubbed pyridine–containing compounds (5a-o) and tested for their antibacterial and antifungal activities for the development of potential antimicrobial agents. The structures of this novel series were chara

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).

Synthesis, characterization, anticancer and in silico studies of a pyrazole-tethered thiazolidine-2,4-dione derivative

A new pyrazole-tethered thiazolidine-2,4-dione derivative (8) has been synthesized by the Knoevenagel condensation of 3-(4-nitrophenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde (4) and 3-(2,4-dioxothiazolidin-3-yl)propanenitrile (7). The structure of the final

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.].

In vitro studies of potent aldose reductase inhibitors: Synthesis, characterization, biological evaluation and docking analysis of rhodanine-3-hippuric acid derivatives

Inhibitors of aldose reductase are rate-limiting enzymes and could play a key role to prevent the complications of diabetes. In our attempt to develop novel inhibitors of aldose reductase, the derivatives of rhodanine-3-hippuric acid-pyrazole hybrid were synthesized and characterised by spectral data. The biological studies reveal that all the compounds show an excellent activity against ALR2 with IC50 values ranging from 0.04 to 1.36 μM. Among these the synthesised compounds 6a-m, 6g and 6e showed specific inhibitory activity with IC50 values of 0.04 and 0.06 μM respectively against ALR2 and found to be more potent than epalrestat (IC50 = 0.87 μM), the only aldose reductase inhibitor currently used in the therapy. Molecular docking analysis using the AR-NADP+ complex as a receptor was performed with all the synthesized compounds. All the compounds exhibit a well-defined binding mode within the AR active site, similarly to previous described AR inhibitors, with the anion head group bound to the catalytic center, blocking thus its activity. By forming hydrogen bonds with Tyr48 and His110 of the protein from ALR2 (PDB ID: 2FZD), the compounds 6g and 6e interrupt the proton donation mechanism, which is necessary for the catalytic activity of ALR2.

Synthesis and computational studies of highly selective inhibitors of human recombinant tissue non-specific alkaline phosphatase (h-TNAP): A therapeutic target against vascular calcification

In this study, we have discovered small druglike molecules as selective inhibitors of human tissue-nonspecific alkaline phosphatase (h-TNAP), an enzyme critical for the regulation of extracellular matrix calcification. The upregulation of h-TNAP is associated with various pathologies particularly the vascular calcification (VC). Selective inhibition of h-TNAP over h-NPP1 may serve as a useful therapeutic strategy against vascular calcification. A series of novel triazolyl pyrazole derivatives (10a-y) in which thiol bearing triazole moiety as the zinc binding functional group was introduced to a pyrazole based pharmacophore was synthesized and evaluated as potent and selective inhibitors of h-TNAP over h-NPP1. The biological screening against h-TNAP, h-IAP, h-NPP1 and h-NPP3 showed that many of the synthesized compounds are selective inhibitors of TNAP. Particularly, the compounds 10a-h, 10j, 10m-q, 10u, 10w and 10x displayed high potency and complete selectivity towards h-TNAP over h-NPP1. Compound 10q emerged as a highly potent inhibitor (IC50 = 0.16 μM or 160 nM) against h-TNAP with 127-fold increased inhibition compared to levamisole. On the other hand, compound 10e was found to be most selective inhibitor against the tested APs and NPPs (IC50 = 1.59 ± 0.36 μM). Binding sites architecture analysis, molecular-docking and molecular dynamics simulations (MDS), revealed the basis for h-TNAP and h-IAP ligand selectivity as well as selectivity towards h-TNAP over h-NPP1. These newly discovered inhibitors are believed to represent valuable lead structures to further streamline the generation of candidate compounds to target VC.

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