19652-14-3

Usage

Uses

Used in Pharmaceutical Industry:
5-(4-CHLORO-PHENYL)-2-PHENYL-2H-PYRAZOL-3-YLAMINE is used as a reactant in the preparation of trifluoromethyl-substituted pyrazolo[3,4-b]pyridines. These compounds are of interest due to their antimicrobial properties, making them potentially useful in the development of new drugs to combat various types of infections.
Used in Chemical Synthesis:
In the field of chemical synthesis, 5-(4-CHLORO-PHENYL)-2-PHENYL-2H-PYRAZOL-3-YLAMINE can serve as a building block or intermediate for the creation of more complex molecules with diverse applications. Its unique structure allows for further functionalization and modification, which can lead to the development of new compounds with specific properties and uses.
Used in Research and Development:
Due to its structural features, 5-(4-CHLORO-PHENYL)-2-PHENYL-2H-PYRAZOL-3-YLAMINE may be utilized in research and development for various purposes, such as studying its chemical reactivity, exploring its potential as a precursor to other compounds, or investigating its biological activities. This can contribute to the advancement of knowledge in the fields of chemistry, biology, and materials science.

InChI:InChI=1/C15H12ClN3/c16-12-8-6-11(7-9-12)14-10-15(17)19(18-14)13-4-2-1-3-5-13/h1-10H,17H2

Upstream product

• 100-63-0 phenylhydrazine 
• 4640-66-8 p-chlorobenzoylacetonitrile 
• 7335-27-5 ethyl 4-chlorobenzoate 
• 536-38-9 4-chlorobenzoylmethyl bromide 
• 99-91-2 para-chloroacetophenone 

Downstream Products

• 851052-51-2 [5-(4-chloro-phenyl)-2-phenyl-2H-pyrazol-3-yl]-thiourea 
• 873913-39-4 5-amino-3-(4-chlorophenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde 

Relevant academic research and scientific papers

Highly Efficient Chemoselective Synthesis of Pyrrolo[2,3- c ]pyrazole Bearing Oxindole via Sequential Condensation-Michael Addition-Intramolecular Cyclization Reactions

An efficient and highly chemoselective approach for the synthesis of novel scaffolds based on pyrrolo[2,3- c ]pyrazole bearing oxindole is accomplished by the acid-promoted sequential reactions between benzoylacetonitriles, phenylhydrazine, and 3-phenacyl

Synthesis and in vitro antiproliferative activity of certain novel pyrazolo[3,4-b]pyridines with potential p38α MAPK-inhibitory activity

Novel series of pyrazolo[3,4-b]pyridines 9a–j and 14a–f were prepared via a one-pot three-component reaction. Compounds 9a–j were synthesized by the reaction of 3-(4-chlorophenyl)?1-phenyl-1H-pyrazol-5-amine (4) with benzoyl acetonitriles 3a,b and aldehydes 5a–e, whereas the spiro derivatives 14a–f were synthesized by the reaction of pyrazole derivative 4 with 3a–c and indoline-2,3-diones 10a,b. Screening of the antiproliferative activity of 9a–j and 14a–f revealed that 14a and 14d were the most potent analogues against HepG2 and HeLa cells, with IC50 = 4.2 and 5.9 μM, respectively. Moreover, compounds 9c and 14a could promote cell cycle disturbance and apoptosis in HepG2 cells, as evidenced by DNA flow cytometry and Annexin V-FITC/PI assays. Cell cycle analysis of 9c and 14a indicated a reduction in HepG2 cells in the G1 phase, with arrest in the S phase and the G2/M phase, respectively. Also, 9c and 14a are good apoptotic inducers in the HepG2 cell line. Furthermore, compounds 9h and 14d stood out as the most efficient antiproliferative agents in the NCI 60-cell line panel screening, with mean GI % equal to 60.3% and 55.4%, respectively. Additionally, 9c, 9h, 14a, and 14d showed good inhibitory action against the cellular pathway regulator p38α kinase, with IC50 = 0.42, 0.41, 0.13, and 0.64 μM, respectively. A docking study was carried out on the p38α kinase active site, showing a binding mode comparable to that of reported p38 mitogen-activated protein kinase inhibitors. These newly discovered pyrazolo[3,4-b]pyridines could be considered as potential candidates for the development of newly targeted anticancer agents.

Phenyl pyrazole compound, pharmaceutical composition and preparation method and application of phenyl pyrazole compound

The invention discloses a phenyl pyrazole compound, a pharmaceutical composition and a preparation method and application of the phenyl pyrazole compound. The phenyl pyrazole compound shown in a formula I or a formula II can be used for preparing drugs fo

Microwave synthesis of 1-aryl-1H-pyrazole-5-amines

A microwave-mediated synthesis of 1H-pyrazole-5-amines utilizing 1 M HCl at 150 °C was developed in order to provide products in a matter of minutes with minimal purification. Most reactions are complete in only 10 min and can be isolated via a simple filtration without the need for further purification by column chromatography or recrystallization. This method tolerates a range of functional groups and can be performed on milligram to gram scales.

"On-Water" Facile Synthesis of Novel Pyrazolo[3,4-b]pyridinones Possessing Anti-influenza Virus Activity

A facile and versatile "on-water" protocol for the synthesis of pyrazolo[3,4-b]pyridinones was developed by the unprecedented construction of two rings and five new bonds in one-pot. It was proved that water was an important promoter of the reaction and P

Pyridino-pyrazolon derivative and application thereof medicine against anti-influenza-a virus

The invention provides a pyridino-pyrazolon derivative and application thereof in a medicine against influenza a virus. The pyridino-pyrazolon derivative is provided and named a compound J1. A series of studies find that the compound J1 has remarkable act

Synthesis and biological evaluation of pyrazolo[3,4-b]pyridin-4-ones as a new class of topoisomerase II inhibitors

A series of 1,3,6-triphenylpyrazolo[3,4-b]pyridin-4-one derivatives was designed, synthesized and evaluated for cytotoxic activity in A375 human melanoma and human erythroleukemia (HEL) cells. The new pyrazolopyridones displayed comparable activities to the antitumor compound etoposide. The inhibitory effect of compounds 17, 18, 27 and 32 against topoisomerase II-mediated cleavage activities was measured finding good correlation with the results obtained from MTS assay. Docking studies into bacterial topoisomerase II (DNA Gyrase), topoisomerase IIα and topoisomerase IIβ binding sites in the DNA binding interface were performed.

Design, synthesis, and biological activity of urea derivatives as anaplastic lymphoma kinase inhibitors

In anaplastic large-cell lymphomas, chromosomal translocations involving the kinase domain of anaplastic lymphoma kinase (ALK), generally fused to the 5' part of the nucleophosmin gene, produce highly oncogenic ALK fusion proteins that deregulate cell cycle, apoptosis, and differentiation in these cells. Other fusion oncoproteins involving ALK, such as echinoderm microtubule-associated protein-like 4-ALK, were recently found in patients with non-small-cell lung, breast, and colorectal cancers. Recent research has focused on the development of inhibitors for targeted therapy of these ALK-positive tumors. Because kinase inhibitors that target the inactive conformation are thought to be more specific than ATP-targeted inhibitors, we investigated the possibility of using two known inhibitors, doramapimod and sorafenib, which target inactive kinases, to design new urea derivatives as ALK inhibitors. We generated a homology model of ALK in its inactive conformation complexed with doramapimod or sorafenib in its active site. The results elucidated why doramapimod is a weak inhibitor and why sorafenib does not inhibit ALK. Virtual screening of commercially available compounds using the homology model of ALK yielded candidate inhibitors, which were tested using biochemical assays. Herein we present the design, synthesis, biological activity, and structure-activity relationships of a novel series of urea compounds as potent ALK inhibitors. Some compounds showed inhibition of purified ALK in the high nanomolar range and selective antiproliferative activity on ALK-positive cells.

Synthesis of 3-(N-1,3-diarylpyrazol-5-yl)amino-2H-[1,4]-benzoxa/thiazines and 3-(N-1,3-diarylpyrazol-5-yl)iminomethyl chromones

A series of new 3-(N-1,3-diarylpyrazol-5-yl)amino-2H-[1,4]-benzoxa/ thiazines (4a-c, 5a & 6a-c) and 3-(N-1,3-diarylpyrazol-5-yl)iminomethyl chromones (8a-e) have been synthesized from 5-amino-1,3-diarylpyrazoles (1).