5399-92-8

Basic information

• Product Name: 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine
• Synonyms: IFLAB-BB F0909-0060;4-CHLORO-1H-PYRAZOLO3,4-DPYRIMIDINE;AKOS BBS-00002106;4-Chloropyrazolo[3,4-d]pyrimidine;NSC 4937;1H-Pyrazolo[3,4-d]pyrimidine, 4-chloro-;4-chloro-1H-pyrazolo[3;4-Chlor-1(2)Hpyrazolo[3,4-d]pyriMidine
• CAS NO: 5399-92-8
• Molecular Formula: C₅H₃ClN₄
• Molecular Weight: 154.56
• EINECS: 1592732-453-0
• Product Categories: Halides;Bases & Related Reagents;Heterocycles;Inhibitors;Nucleotides;Fused Ring Systems;Heterocycle-Pyrimidine series
• Mol File: 5399-92-8.mol
• Article Data: 35

Chemical Properties

• Melting Point: >350?C
• Boiling Point: 348.315 °C at 760 mmHg
• Flash Point: 195.349 °C
• Appearance: /
• Density: 1.653 g/cm³
• Vapor Pressure: 7.5E-08mmHg at 25°C
• Refractive Index: 1.739
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly, Sonicated)
• PKA: 10.16±0.20(Predicted)
• CAS DataBase Reference: 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine(5399-92-8)
• EPA Substance Registry System: 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine(5399-92-8)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 5399-92-8(Hazardous Substances Data)

Usage

Description

4-Chloro-1H-pyrazolo[3,4-d]pyrimidine is a chemical compound belonging to the class of pyrazolopyrimidines. It is characterized by the presence of a chlorine atom at the 4th position and a pyrimidine ring fused to a pyrazole ring. This pale yellow solid exhibits unique chemical properties and has been found to possess a SK channel blocker effect, which is significant in various applications.

Uses

Used in Pharmaceutical Industry:
4-Chloro-1H-pyrazolo[3,4-d]pyrimidine is used as a SK channel blocker for its potential role in the development of therapeutic agents targeting ion channels. The SK channel blocker effect of this compound makes it a promising candidate for the treatment of various conditions, such as neurological disorders and cardiovascular diseases, where ion channel modulation is crucial.
Used in Chemical Research:
As a chemical compound with distinct properties, 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine is also used in chemical research for the synthesis of novel molecules and the exploration of new chemical reactions. Its unique structure and functional groups make it an interesting starting point for the development of new compounds with potential applications in various fields.
Used in Material Science:
The pale yellow solid nature of 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine may also find applications in material science, particularly in the development of new materials with specific optical, electronic, or mechanical properties. 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine's chemical structure and properties can be exploited to create novel materials with tailored characteristics for various industrial applications.

InChI:InChI=1/C5H3ClN4/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H,7,8,9,10)

Upstream product

• 315-30-0 Allopurinol 
• 315-30-0 4-hydroxypyrazolo(3,4-d)pyrimidine 
• 5305-40-8 2,6-dichloro-pyrimidine carbaldehyde 
• 2644-70-4 hydrazine hydrochloride 
• 13877-55-9 pyrazolo<4,3-d>pyrimidin-7-one 
• 7803-57-8 hydrazine hydrate 
• 184789-03-5 1,2-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one 
• 916980-04-6 allopurinol 

Downstream Products

• 56964-92-2 (3-methyl-butyl)-(1⁽²⁾H-pyrazolo[3,4-d]pyrimidin-4-yl)-amine 
• 6288-97-7 ethyl-propyl-(1⁽²⁾H-pyrazolo[3,4-d]pyrimidin-4-yl)-amine 
• 32353-19-8 4-ethoxy-1⁽²⁾H-pyrazolo[3,4-d]pyrimidine 
• 5405-64-1 isopropyl-(1⁽²⁾H-pyrazolo[3,4-d]pyrimidin-4-yl)-amine 
• 102353-67-3 N,N-diethyl-N'-(1⁽²⁾H-pyrazolo[3,4-d]pyrimidin-4-yl)-ethylenediamine 
• 99973-41-8 N-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 6284-74-8 methyl-(1⁽²⁾H-pyrazolo[3,4-d]pyrimidin-4-yl)-amine 
• 5470-54-2 4-ethylsulfanyl-1⁽²⁾H-pyrazolo[3,4-d]pyrimidine 
• 5334-23-6 4-Mercapto-1H-pyrazolo<3,4-d>pyrimidine 
• 271-80-7 1H-pyrazolo[3,4-d]pyrimidine 
• 2380-63-4 4-Aminopyrazolo<3,4-d>pyrimidin 
• 5399-93-9 4-methoxy-1H-pyrazolo[3,4-d]-pyrimidine 
• 82859-61-8 C₁₄H₂₁N₆O 
• 82859-62-9 C₁₅H₂₃N₆O 

Relevant articles and documents

Design, synthesis, biological evaluation and molecular modeling of novel 1H-pyrazolo[3,4-d]pyrimidine derivatives as BRAFV600E and VEGFR-2 dual inhibitors

Aiming to explore novel BRAFV600E and VEGFR-2 dual inhibitors, a series of 1H-pyrazolo[3,4-d]pyrimidine derivatives were designed, synthesized and biologically evaluated in this study. Most of the synthesized 1H-pyrazolo[3,4-d]pyrimidine compounds displayed moderate to high potent activity in both enzymatic and cellular proliferation assays. Among these compounds, 9e, 9g, 9m and 9u showed remarkably high inhibitory activities against both BRAFV600E and VEGFR-2 kinase comparable to positive control Sorafenib. Particularly, compound 9u also showed potent anti-proliferative activity against BRAFV600E-expressing A375 (IC50 = 1.74 μM) and H-29 (IC50 = 6.92 μM) as well as VEGFR-2-expressing HUVEC (IC50 = 5.89 μM), which was also comparable to Sorafenib. Furthermore, kinase selectivity profile showed that 9u had almost poor or no significant inhibitory activity against wild-type BRAF and 15 other tested protein kinases. Flow cytometric analysis showed that compound 9u mainly arrested the A375 and HUVEC cell lines in the G0/G1 stage with a concentration-dependent effect. In addition, the molecular docking and molecular dynamics simulations suggested that 9u adopted a similar binding pattern with Sorafenib at the ATP-binding sites of BRAFV600E and VEGFR-2. Taken together, these results indicated that compound 9u may serve as novel lead compound in research on more effective BRAFV600E and VEGFR-2 dual inhibitors.

(1H-pyrazolo[3,4-d]pyrimidine)-4-amino derivative and application of same as IDO inhibitor to drug preparation

The invention discloses a (1H-pyrazolo[3,4-d]pyrimidine)-4-amino derivative and a preparation method thereof, and application of the derivative as an IDO inhibitor. The derivative provided by the invention can be used for preventing and/or treating a plurality of diseases, such as Alzheimer's disease, cataract, infections related to cellular immune activation, autoimmune diseases, AIDS, cancers, depression or metabolic disorder of tryptophan.

1-(2-tetrahydropyrane)-1H-pyrazole[3, 4-d] pyrimidine compound having anti-tumor activity and preparation method thereof

The invention discloses a 1-(2-tetrahydropyrane)-1H-pyrazole[3, 4-d] pyrimidine compound having anti-tumor activity. A general formula of the compound is shown as follows. The invention further discloses a synthesis method of the compound and a medicinal composition containing the compound. The invention further discloses application of the medicinal composition in treating diseases caused by protein kinase activity abnormality. The pyrazole [3, 4-d] pyrimidine compound which is novel in structure and remarkable in anti-tumor activity is developed. The compound can be used as a double-target inhibitor of BRAF/VEGFR-2 kinase and has good effect and wide application prospect in the aspect of treating the diseases caused by protein kinase activity abnormality.