289651-72-5

Basic information

• Product Name: 1-(4-fluorophenyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one
• Synonyms: 1-(4-fluorophenyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one
• CAS NO: 289651-72-5
• Molecular Formula: C₁₁H₇FN₄O
• Molecular Weight: 230.1978832
• Mol File: 289651-72-5.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 416.6±51.0 °C(Predicted)
• Appearance: /
• Density: 1.54±0.1 g/cm3(Predicted)
• PKA: -2.06±0.20(Predicted)
• CAS DataBase Reference: 1-(4-fluorophenyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-fluorophenyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one(289651-72-5)
• EPA Substance Registry System: 1-(4-fluorophenyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one(289651-72-5)

Safety Data

• Hazardous Substances Data: 289651-72-5(Hazardous Substances Data)

Usage

Description

1-(4-fluorophenyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one is a chemical compound belonging to the class of pyrazolopyrimidines. It is characterized by its unique molecular structure, which features a pyrazolo[3,4-d]pyrimidin-4-one core with a 4-fluorophenyl group attached to the first position. 1-(4-fluorophenyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one has garnered significant interest due to its potential applications in various fields, particularly in the pharmaceutical industry.

Uses

Used in Pharmaceutical Industry:
1-(4-fluorophenyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one is used as a key intermediate in the synthesis of pyrrole and pyrazolopyrimidines. These synthesized compounds serve as inhibitors of ubiquitin-specific protease 7 (USP7), which plays a crucial role in the treatment of various diseases.
Used in Cancer Treatment:
As an inhibitor of USP7, 1-(4-fluorophenyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one contributes to the development of therapeutic agents for the treatment of cancers. USP7 inhibition has been linked to the suppression of tumor growth and the prevention of cancer progression.
Used in Neurodegenerative Disease Treatment:
1-(4-fluorophenyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one is also utilized in the development of treatments for neurodegenerative diseases, such as Alzheimer's, Parkinson's, and Huntington's disease. USP7 inhibition has been shown to have potential neuroprotective effects, which can help in managing the symptoms and progression of these diseases.
Used in Immunology Disorder Treatment:
1-(4-fluorophenyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one is employed in the synthesis of compounds that target USP7, which is involved in the regulation of immune responses. Inhibiting USP7 can help in the development of treatments for immunology disorders, such as autoimmune diseases and inflammatory conditions.
Used in Inflammatory Disorder Treatment:
1-(4-fluorophenyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one is used in the development of anti-inflammatory drugs by targeting USP7. Inhibition of this protease can help in reducing inflammation and managing the symptoms of inflammatory disorders.
Used in Cardiovascular Disease Treatment:
1-(4-fluorophenyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one is utilized in the synthesis of compounds that can help in the treatment of cardiovascular diseases. USP7 inhibition has been linked to the regulation of vascular function and the prevention of atherosclerosis.
Used in Ischemic Disease Treatment:
1-(4-fluorophenyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one is used in the development of therapeutic agents for the treatment of ischemic diseases, such as stroke and myocardial infarction. USP7 inhibition can help in reducing the damage caused by ischemic events and improving the recovery process.
Used in Antiviral and Antibacterial Applications:
1-(4-fluorophenyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one is employed in the synthesis of compounds with antiviral and antibacterial properties. USP7 inhibition can help in the development of treatments for viral infections and diseases, as well as bacterial infections and diseases.

Upstream product

• 77287-34-4 formamide 
• 51516-69-9 5-amino-1-(4-fluorophenyl)-1H-pyrazole-4-carboxamide 
• 64-18-6 formic acid 
• 51516-70-2 5-amino-1-(4-fluorophenyl)-1H-pyrazole-4-carbonitrile 
• 371-14-2 4-fluorophenylhydrazine 
• 122-51-0 orthoformic acid triethyl ester 

Downstream Products

• 885524-07-2 4-chloro-1-(4-fluorophenyl)-1H-pyrazolo[3,4-d]pyrimidine 
• 1392411-82-3 5-(2,2-diethoxyethyl)-1-(4-fluorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one 
• 1234320-83-2 5-[2-(3-chlorophenyl)-2-oxoethyl]-1-(4-fluorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one 
• 1234320-89-8 7-(3-chlorophenyl)-1-(4-fluorophenyl)-5,6-dihydropyrazolo[3,4-e][1,4]diazepin-4(1H)-one 
• 1234320-78-5 5-amino-N-(2,2-diethoxyethyl)-1-(4-fluorophenyl)-1H-pyrazole-4-carboxamide 
• 1234320-81-0 1-(4-fluorophenyl)-7-hydroxy-5,6,7,8-tetrahydropyrazolo[3,4-e][1,4]diazepin-4(1H)-one 
• 1234320-72-9 2-[5-amino-1-(4-fluorophenyl)-1H-pyrazol-4-ylcarbonylamino]acetic acid 
• 1234320-76-3 1-(4-fluorophenyl)-1,5,6,8-tetrahydropyrazolo-[3,4-e][1,4]diazepine-4,7-dione 

Relevant articles and documents

Piperidine compound and preparation method and medical application thereof

The invention discloses a piperidine compound shown as a formula (I) and a preparation method and medical application thereof, and particularly relates to a piperidine USP7 inhibitor compound or pharmaceutically acceptable salt or ester or solvate thereof and a preparation method and application of the piperidine USP7 inhibitor compound or pharmaceutically acceptable salt or ester or solvate thereof. The compound provided by the invention can inhibit the activity of USP7 enzyme, has very good selectivity and druggability, and can be used for preparing medicines for preventing or treating tumor diseases or virus infectious diseases.

New pyrazolopyrimidine derivatives as Leishmania amazonensis arginase inhibitors

Arginase performs the first enzymatic step in polyamine biosynthesis in Leishmania and represents a promising target for drug development. Polyamines in Leishmania are involved in trypanothione synthesis, which neutralize the oxidative burst of reactive oxygen species (ROS) and nitric oxide (NO) that are produced by host macrophages to kill the parasite. In an attempt to synthesize arginase inhibitors, six 1-phenyl-1H-pyrazolo[3,4-d]pyrimidine derivatives with different substituents at the 4-position of the phenyl group were synthesized. All compounds were initially tested at 100 μM concentration against Leishmania amazonensis ARG (LaARG), showing inhibitory activity ranging from 36 to 74%. Two compounds, 1 (R=H) and 6 (R=CF3), showed arginase inhibition >70% and IC50 values of 12 μM and 47 μM, respectively. Thus, the kinetics of LaARG inhibition were analyzed for compounds 1 and 6 and revealed that these compounds inhibit the enzyme by an uncompetitive mechanism, showing Kis values, and dissociation constants for ternary complex enzyme-substrate-inhibitor, of 8.5 ± 0.9 μM and 29 ± 5 μM, respectively. Additionally, the molecular docking studies proposed that these two uncompetitive inhibitors interact with different LaARG binding sites, where compound 1 forms more H-bond interactions with the enzyme than compound 6. These compounds showed low activity against L. amazonensis free amastigotes obtained from mice lesions when assayed with as much as 30 μM. The maximum growth inhibition reached was between 20 and 30% after 48 h of incubation. These results suggest that this system can be promising for the design of potential antileishmanial compounds.

Identification of novel GLUT inhibitors

The compound class of 1H-pyrazolo[3,4-d]pyrimidines was identified using HTS as very potent inhibitors of facilitated glucose transporter 1 (GLUT1). Extensive structure–activity relationship studies (SAR) of each ring system of the molecular framework was established revealing essential structural motives (i.e., ortho-methoxy substituted benzene, piperazine and pyrimidine). The selectivity against GLUT2 was excellent and initial in vitro and in vivo pharmacokinetic (PK) studies are encouraging.