5334-48-5

Basic information

• Product Name: 4-CHLORO-1-PHENYL-1H-PYRAZOLO[3,4-D]PYRIMIDINE
• Synonyms: 4-chloro-1-phenyl-pyrazolo[3,4-d]pyrimidine;4-chloro-1-phenylpyrazolo[3,4-d]pyrimidine;NSC 1425
• CAS NO: 5334-48-5
• Molecular Formula: C₁₁H₇ClN₄
• Molecular Weight: 230.66
• Mol File: 5334-48-5.mol
• Article Data: 33

Chemical Properties

• Boiling Point: 323.7°Cat760mmHg
• Flash Point: 149.6°C
• Appearance: /
• Density: 1.45g/cm³
• Vapor Pressure: 0.000257mmHg at 25°C
• Refractive Index: 1.731
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• CAS DataBase Reference: 4-CHLORO-1-PHENYL-1H-PYRAZOLO[3,4-D]PYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-1-PHENYL-1H-PYRAZOLO[3,4-D]PYRIMIDINE(5334-48-5)
• EPA Substance Registry System: 4-CHLORO-1-PHENYL-1H-PYRAZOLO[3,4-D]PYRIMIDINE(5334-48-5)

Safety Data

• Hazardous Substances Data: 5334-48-5(Hazardous Substances Data)

Usage

General Description

4-CHLORO-1-PHENYL-1H-PYRAZOLO[3,4-D]PYRIMIDINE is a chemical compound with the molecular formula C14H8ClN5. It is a heterocyclic compound containing a pyrazolopyrimidine ring system with a chloro and phenyl substituent. 4-CHLORO-1-PHENYL-1H-PYRAZOLO[3,4-D]PYRIMIDINE is widely used in biochemical research and drug development due to its potential pharmacological activities, including anticancer, antifungal, and anti-inflammatory properties. Its unique structure and reactivity make it a valuable compound for medicinal chemistry, and it is often used as a building block in the synthesis of new pharmaceutical compounds. Additionally, 4-CHLORO-1-PHENYL-1H-PYRAZOLO[3,4-D]PYRIMIDINE has shown potential as a protein kinase inhibitor and has been studied for its potential in treating various diseases and conditions.

InChI:InChI=1/C11H7ClN4/c12-10-9-6-15-16(11(9)14-7-13-10)8-4-2-1-3-5-8/h1-7H

Upstream product

• 21314-17-0 4-hydroxy-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine 
• 21314-17-0 1-phenyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one 
• 5334-43-0 5-Amino-4-cyano-1-phenylpyrazole 
• 100-63-0 phenylhydrazine 
• 5305-40-8 2,6-dichloro-pyrimidine carbaldehyde 
• 1383927-17-0 (E)-(4-chloro-6-(phenylamino)pyrimidin-5-yl)methyleneaminooxysulfonic acid 
• 14160-96-4 4-chloro-6-(phenylamino)pyrimidine-5-carbaldehyde 
• 62-53-3 aniline 
• 16078-71-0 ethyl 5-amino-1-phenyl-1H-pyrazole-4-carboxylate 
• 77287-34-4 formamide 
• 50427-77-5 5-amino-1-phenyl-1H-pyrazole-4-carboxamide 
• 1429924-37-7 4,6-dichloro-5-((2-phenylhydrazono)methyl)pyrimidine 
• 59-88-1 phenylhydrazine hydrochloride 

Downstream Products

• 68380-50-7 4-methoxy-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine 
• 68380-53-0 N-(phenyl)-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 5334-30-5 1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 6014-07-9 4-mercapto-1-phenyl-1,5-dihydro-1H-pyrazolo[3,4-d]pyrimidine 
• 130235-61-9 (1-Phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-pyridin-3-yl-methanone 
• 59564-01-1 furan-2-yl-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-methanone 
• 130235-58-4 (1-Phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-thiophen-2-yl-methanone 
• 89549-85-9 Benzoic acid cyano-(4-nitro-phenyl)-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-methyl ester 
• 89549-77-9 Benzoic acid cyano-phenyl-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-methyl ester 
• 89549-81-5 Benzoic acid (4-chloro-phenyl)-cyano-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-methyl ester 
• 59563-95-0 (1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-p-tolyl-methanone 
• 89549-55-3 (4-Fluoro-phenyl)-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-methanone 
• 59563-90-5 (4-chloro-phenyl)-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-methanone 
• 59563-88-1 (2-chloro-phenyl)-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-methanone 

Relevant articles and documents

ECTONUCLEOTIDE PYROPHOSPHATASE/PHOSPHODIESTERASE 1 (ENPP1) MODULATORS AND USES THEREOF

Provided herein are small molecule modulators of ectonucleotide pyrophosphatase/phosphodiesterase 1 (ENPP1), compositions comprising the compounds, and methods of using the compounds and compositions comprising the compounds.

Ultrasonic-Assisted Synthesis of Pyrazolo[3,4-d]pyrimidin-4-ol Tethered with 1,2,3-Triazoles and Their Anticancer Activity

Abstract: In the presents work synthesis and characterization of new heterocyclic derivatives containing pyrazolo[3,4-d]pyrimidine linkage with 1,4-disubstituted-1,2,3-triazoles via methylene-oxy group. The selected synthesized compounds were tested for their in-vitro anticancer activity against various cancer cell lines. Synthesis of compounds was done under ultrasonic-assisted Huisgen 1,3-dipolar cycloaddition reaction with good yields. Some of the newly synthesized compounds demonstrated good to moderate anticancer activity, most of compounds shows activity against renal cancer cell lines.

Synthesis, evaluation and docking of novel pyrazolo pyrimidines as potent p38α MAP kinase inhibitors with improved anti-inflammatory, ulcerogenic and TNF-α inhibitory properties

A series of nine new N-substituted-4-((1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)amino)benzamides (6a-i) derivatives was synthesized. All the compounds were screened in-vitro for BSA anti-denaturation property, antioxidant assay and p38α MAP kinase inhibition. The in vitro anti-inflammatory assay results revealed that the compounds (6f-i) showed better activity than the compounds 6a-e. Compound 6f bearing the 4-chlorophenyl group showed in vitro anti-inflammatory activity (82.35 ± 4.04) comparable to standard drug diclofenac sodium (84.13 ± 1.63) and better p38α MAP kinase inhibitory activity (IC50 = 0.032 ± 1.63 μM) than the prototypic inhibitor SB203580 (IC50 = 0.041 ± 1.75 μM). The selected active compounds (6f-i) were further studied in animal models for anti-inflammatory activity, ulcerogenic liability, lipid peroxidation and TNF-α inhibition potential. Compound 6f showed promising anti-inflammatory potential with a percentage inhibition of 83.73% when compared to the standard, diclofenac sodium (78.05%). Compound 6f was also found to show reduced ulcerogenic liability and lipid peroxidation in comparison to the standard. This compound also potently inhibited the lipopolysaccharide (LPS)-induced TNF-α production in mice model (ID50 = 8.23 mg/kg) in comparison to SB 203580 (ID50 = 26.38 mg/kg). The molecular docking of compounds 6a-i against p38α MAP kinase receptor was also performed to understand ligand receptor interaction. Amongst all synthesized molecules compound 6f displayed highest docking score of ?9.824. It showed hydrogen bonding interactions with Asn115 and pi-cation interaction with Lys53.