19541-95-8

Usage

Uses

Used in Pharmaceutical and Medicinal Research:
5-Amino-3-(4-methoxyphenyl)pyrazole is utilized as an active pharmaceutical ingredient for its enzyme and receptor inhibitory properties, which are crucial in the development of new drugs targeting a range of diseases.
Used in Cancer Treatment:
In the field of oncology, 5-Amino-3-(4-methoxyphenyl)pyrazole is employed as a potential therapeutic agent, leveraging its capacity to interfere with mechanisms that contribute to cancer progression and survival of cancer cells.
Used in Organic Dyes and Pigments Development:
5-Amino-3-(4-methoxyphenyl)pyrazole is also used as a precursor or component in the synthesis of organic dyes and pigments, capitalizing on its chemical structure to create compounds with specific color and stability properties for various industrial applications.

InChI:InChI=1/C10H11N3O/c1-14-8-4-2-7(3-5-8)9-6-10(11)13-12-9/h2-6H,1H3,(H3,11,12,13)

Upstream product

• 90799-51-2 2-Chlor-3-<4-methoxy-phenyl>-acrylnitril 
• 35070-82-7 2-(4-methoxyphenyl)-3-oxopropanenitrile 
• 123-11-5 4-methoxy-benzaldehyde 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 55991-65-6 [1-(4-methoxyphenyl)vinyloxy]trimethylsilane 
• 138175-63-0 (Z)-3-Bromo-2-ethylsulfanyl-3-(4-methoxy-phenyl)-acrylonitrile 
• 121-98-2 methyl 4-methoxybenzoate 
• 3672-47-7 3-oxo-3-(4'-methoxyphenyl)propanenitrile 
• 57466-68-9 3-chloro-3-(4-methoxyphenyl)acrylonitrile 
• 14063-79-7 3-chloro-3-(4-methoxyphenyl)acrylaldehyde 
• 3672-48-8 5-(4-methoxyphenyl)-1,2-oxazole 

Downstream Products

• 1040725-00-5 C₁₆H₂₀BrN₃O₂ 
• 1040724-60-4 5-bromo-pentanoic acid [5-(4-methoxy-phenyl)-1H-pyrazol-3-yl]-amide 
• 1040724-60-4 5-bromo-pentanoic acid [5-(4-methoxy-phenyl)-1H-pyrazol-3-yl]-amide 
• 1245236-07-0 C₂₂H₁₉Cl₂N₃O₃ 
• 1258222-95-5 C₂₈H₃₁N₉O₂S 
• 1159982-73-6 5,7-dichloro-2-(4-methoxy-phenyl)-pyrazolo[1,5-a]pyrimidine 
• 1232220-39-1 N-{2-(4-methoxy-phenyl)-7-morpholin-4-yl-pyrazolo[1,5-a]pyrimidin-5-yl}-N-(3-methyl-benzylidene)-hydrazine 
• 1232223-29-8 5-chloro-2-(4-methoxy-phenyl)-7-morpholin-4-yl-pyrazolo[1,5-a]pyrimidine 

Relevant academic research and scientific papers

Synthesis of some novel fluorinated pyrazolo[3,4-b]pyridines

Reaction of 5-amino-3-substituted pyrazoles (1a-c) and 5-amino-1,3- disubstituted pyrazoles (1d-i) with fluorinated-β-diketones (2) results in the formation of the single isomer of pyrazolo[3,4-b]pyridines (4a-h). A one-pot procedure for the synthesis of

New synthesis of 3-aryl-5-amino-1H-pyrazoles

A new efficient procedure has been proposed for the synthesis of 3-aryl-5-amino-1H-pyrazoles by reaction of α-chloro-β- arylacrylonitriles with hydrazine hydrate.

Novel benzenesulfonamide-bearing pyrazoles and 1,2,4-thiadiazoles as selective carbonic anhydrase inhibitors

Two series comprising 20 novel benzenesulfonamides bearing thioureido-linked pyrazole 8 and amino-1,2,4-thiadiazole 10 were synthesized and assayed as human carbonic anhydrase (hCA) inhibitors against isoforms I and II as well as the tumor-associated isof

Modular synthesis and antiproliferative activity of new dihydro-1H-pyrazolo[1,3-b]pyridine embelin derivatives

A set of new dihydro-1H-pyrazolo[1,3-b]pyridine and pyrazolo[1,3-b]pyridine embelin derivatives was synthesized through a multicomponent reaction from natural embelin, 3-substituted-5-aminopyrazoles and aldehydes. The synthesized compounds were evaluated against three hematologic tumor cell lines, HEL (acute erythroid leukemia), K-562 (chronic myeloid leukemia) and HL-60 (acute myeloid leukemia), and five breast cancer cell lines (SKBR3, MCF-7, MDA-MB-231, BT-549, HS-578T). The primate non-malignant kidney Vero cell line was used as the control of cytotoxicity. From the obtained results, some structure–activity relationships were out-lined. Furthermore, in silico prediction of physicochemical properties and ADME parameters were determined for the derivatives with the best antiproliferative values.

Polysubstituted heterocyclic derivative, preparation method thereof and application of polysubstituted heterocyclic derivative in medicine

The invention provides a polysubstituted heterocyclic derivative, a preparation method thereof and application of the polysubstituted heterocyclic derivative in medicine, and belongs to the technical field of medicinal chemistry. The polysubstituted heterocyclic derivative is a compound shown in a general formula I or II, a pharmaceutically acceptable salt or a solvate of the compound, and the compound can inhibit mRNA demethylase on the protease level and is used for treating diseases related to mRNA demethylase functions.

Discovery of 2,4-diaminopyrimidine derivatives targeting p21-activated kinase 4: Biological evaluation and docking studies

In this study, novel 2,4-diaminopyrimidine derivatives targeting p21-activated kinase 4 (PAK4) were discovered and evaluated for their biological activity against PAK4. Among the derivatives studied, promising compounds A2, B6, and B8 displayed the highest inhibitory activities against PAK4 (IC50 = 18.4, 5.9, and 20.4 nM, respectively). From the cellular assay, compound B6 exhibited the highest potency with an IC50 value of 2.533 μM against A549 cells. Some compounds were selected for computational ADME (absorption, distribution, metabolism, and elimination) properties and molecular docking studies against PAK4. The detailed structure–activity relationship based on the biochemical activities and molecular docking studies were explored. According to the docking studies, compound B6 had the lowest docking score (docking energy: ?7.593 kcal/mol). The molecular docking simulation indicated the binding mode between compound B6 and PAK4. All these results suggest compound B6 as a useful candidate for the development of a PAK4 inhibitor.

Synthesis of pyrazolopyrimidinones using a “one-pot” approach under microwave irradiation

A simple one-pot method for the microwave-assisted synthesis of substituted pyrazolo[1,5-a]pyrimidinones, a core scaffold in many bioactive and pharmaceutically relevant compounds, has been established. A variety of substituents was tolerated at the 2 and 5 positions, including functionalized aryls, heterocycles, and alkyl groups.

"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

Fragment-Based Approaches to the Development of Mycobacterium tuberculosis CYP121 Inhibitors

The essential enzyme CYP121 is a target for drug development against antibiotic resistant strains of Mycobacterium tuberculosis. A triazol-1-yl phenol fragment 1 was identified to bind to CYP121 using a cascade of biophysical assays. Synthetic merging and optimization of 1 produced a 100-fold improvement in binding affinity, yielding lead compound 2 (KD = 15 μM). Deconstruction of 2 into its component retrofragments allowed the group efficiency of structural motifs to be assessed, the identification of more LE scaffolds for optimization and highlighted binding affinity hotspots. Structure-guided addition of a metal-binding pharmacophore onto LE retrofragment scaffolds produced low nanomolar (KD = 15 nM) CYP121 ligands. Elaboration of these compounds to target binding hotspots in the distal active site afforded compounds with excellent selectivity against human drug-metabolizing P450s. Analysis of the factors governing ligand potency and selectivity using X-ray crystallography, UV-vis spectroscopy, and native mass spectrometry provides insight for subsequent drug development.

Synthesis of Aminopyrazoles from Isoxazoles: Comparison of Preparative Methods by in situ NMR Analysis

A single-step method and a two-step method for the synthesis of aminopyrazoles from isoxazoles are presented and compared. Based on in situ NMR monitoring, both processes proceed through a ketonitrile. In the single-step process, hydrazine serves to both open the isoxazole to the unisolated ketonitrile intermediate and form the aminopyrazole. The two-step process involves ring opening of the isoxazole by deprotonation with hydroxide to generate the ketonitrile followed by the addition of acetic acid and hydrazine to form the aminopyrazole.