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

Chemical Properties

Pale Yellow Solid

Uses

Different sources of media describe the Uses of 5399-92-8 differently. You can refer to the following data:
1. Has a SK channel blocker effect.
2. Has a SK channel blocker effect

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

Downstream Products

• 1013930-73-8 4-chloro-1-[2-chloro-2-(4-fluorophenyl)ethyl]-1H-pyrazolo[3,4-d]-pyrimidine 
• 1013930-74-9 4-chloro-1-[2-chloro-2-(4-chlorophenyl)ethyl]-1H-pyrazolo[3,4-d]pyrimidine 
• 1283727-48-9 1-[2-chloro-2-(4-fluorophenyl)ethyl]-N-(pyridin-4-ylmethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 1283727-50-3 1-[2-chloro-2-(4-chlorophenyl)ethyl]-N-(pyridin-4-ylmethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 1451010-34-6 (Z)-4-((1-(4-fluorostyryl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)methyl)-5-(hydroxymethyl)-2-methylpyridin-3-ol 
• 1451010-36-8 1-(2-chloro-2-(4-chlorophenyl)ethyl)-N-(4-(4-methylpiperazin-1-yl)benzyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 1451010-31-3 2-(4-(benzylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-(4-fluorophenyl)ethanone 
• 1451010-32-4 2-(4-chloro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-(4-fluorophenyl)ethanol 
• 1451010-33-5 2-(4-chloro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-(4-chlorophenyl)ethanol 
• 1451010-29-9 2-(4-chloro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-(4-fluorophenyl)ethanone 
• 1451010-30-2 2-(4-chloro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-(4-chlorophenyl)ethanone 
• 959430-93-4 4-Chloro-2-pentyl-2H-pyrazolo[3,4-d]pyrimidine 
• 959430-78-5 4-chloro-1-propyl-1H-pyrazolo[3,4-d]pyrimidine 
• 959430-79-6 4-chloro-2-propyl-1H-pyrazolo[3,4-d]pyrimidine 

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.

Structure-metabolism relationships in human-AOX: Chemical insights from a large database of aza-aromatic and amide compounds

Aldehyde oxidase (AOX) is a metabolic enzyme catalyzing the oxidation of aldehyde and aza-aromatic compounds and the hydrolysis of amides, moieties frequently shared by the majority of drugs. Despite its key role in human metabolism, to date only fragmentary information about the chemical features responsible for AOX susceptibility are reported and only "very local" structure-metabolism relationships based on a small number of similar compounds have been developed. This study reports a more comprehensive coverage of the chemical space of structures with a high risk of AOX phase I metabolism in humans. More than 270 compounds were studied to identify the site of metabolism and themetabolite(s). Both electronic [supported by density functional theory (DFT) calculations] and exposure effects were considered when rationalizing the structure-metabolism relationship.

(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.