271-73-8

Usage

Chemical Properties

Pale Orange Solid

Uses

A pyrazole derivative as kinase inhibitors.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 7, p. 247, 1970 DOI: 10.1002/jhet.5570070146

InChI:InChI=1/C6H5N3/c1-2-5-4-8-9-6(5)7-3-1/h1-4H,(H,7,8,9)

Upstream product

• 36404-88-3 2-chloro-3-carbaldehydepyridine 
• 75427-06-4 1‐benzyl‐1H‐pyrazolo[3,4‐b]pyridine 
• 75427-09-7 1-ethyl-1H-pyrazolo<3,4-b>pyridine 
• 63682-42-8 3-Diazapyrazolo<3,4-b>pyridine 
• 75427-15-5 1-benzyl-1H-pyrazolo<3,4-b>pyridine 7-oxide 
• 6752-16-5 1H-pyrazolo[3,4-b]pyridin-3-amine 
• 109-09-1 2-chloropyridine 
• 128071-75-0 2-bromopyridine-3-carboxaldehyde 
• 63682-46-2 C₆H₄N₅⁽¹⁺⁾*BF₄^(1-) 
• 6602-54-6 2-chloro-3-pyridinecarbonitrile 
• 36404-90-7 2-fluoropyridine-3-carboxaldehyde 

Downstream Products

• 619-93-2 4,4'-dinitro stilbene 
• 75427-18-8 1-(4-nitrobenzyl)-1H-pyrazolo<3,4-b>pyridine 
• 116855-10-8 2-benzylpyrazolo<3,4-b>pyridine 
• 116855-16-4 1H-Pyrazolo[3,4-b]pyridine-6-carboxylic acid amide 
• 117007-52-0 3-iodo-1H-pyrazolo[3,4-b]pyridine 
• 1070436-97-3 3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine 
• 1246520-74-0 C₁₇H₁₅N₃O₃ 
• 1246519-54-9 C₁₈H₁₈N₄O₂ 
• 1246519-62-9 C₁₇H₁₇ClN₄O 
• 1246519-71-0 C₁₉H₂₂N₄O 
• 1246519-76-5 C₁₈H₂₀N₄O₂ 
• 1246519-78-7 C₂₂H₂₇N₅O₃ 
• 1246519-79-8 C₂₃H₂₉N₅O₃ 
• 1246520-07-9 C₁₈H₁₉ClN₄O 

Relevant academic research and scientific papers

New 1-hydroxy-1,1-bisphosphonates derived from 1H-Pyrazolo[3,4-b]pyridine: Synthesis and characterization

A number of 1H-pyrazolo[3,4-b]pyridine derivatives, starting from 2-chloro-3-formyl pyridine, was synthesized to obtain new 1- hydroxybisphosphonates, a class of compounds with potential biological interest. Spectroscopic data were used to characterize all compounds and to identify N-1 and N-2 regioisomers, and mono- and bisphosphonates derivatives. X-ray diffractometry studies of compound 7a confirmed the proposed structure.

Novel Bisphosphonates Derived from 1H-Indazole, 1H-Pyrazolo[3,4-b]Pyridine, and 1H-Pyrazolo[3,4-b]Quinoline

Novel tetraethyl ethylene-1,1-bisphosphonate esters derived from 1H-indazole, 1H-pyrazolo[3,4-b]pyridine, and 1H-pyrazolo[3,4-b]quinoline were synthesized by a Michael addition reaction of tetraethyl ethylidene-1,1-bisphosphonate with the corresponding heterocycle, using conventional heating and microwave-assisted methods. The microwave-assisted method provides shorter reaction times and better yields. The hydrolysis of bisphosphonates afforded the corresponding bisphosphonic acids or salt, using concentrated hydrochloric acid or TMSBr/collidine, respectively. All new compounds were fully characterized, and their structures were assigned using 1H, 31P, and 13C NMR and IR spectroscopies and mass spectrometry. The molecular structure of compound 6 was confirmed by X-ray diffraction studies.

A novel copper-catalyzed, hydrazine-free synthesis of N-1 unsubstituted 1H-indazoles using stable guanylhydrazone salts as substrates

A CuI-catalyzed, hydrazine-free transformation of 2-(2-bromoarylidene)guanylhydrazone hydrochlorides using Cs2CO3 as a base and DMEDA as a ligand at 120 °C for 5 h delivers substituted 1H-indazoles with yields up to 75%. The C,N double bond configuration of the substrates was determined by NMR experiments and quantum chemical calculations. The reaction mechanism was studied using quantum chemical calculations.

INHIBITORS OF CYCLIN DEPENDNT KINASE 7 (CDK7)

The present invention provides novel compounds of Formula (I) and pharmaceutically acceptable salts, solvates, hydrates, tautomers, stereoisomers, isotopically labeled derivatives, and compositions thereof. Also provided are methods and kits involving the compounds or compositions for treating or preventing proliferative diseases (e.g., cancers (e.g., leukemia, melanoma, multiple myeloma), benign neoplasms, angiogenesis, inflammatory diseases, autoinflammatory diseases, and autoimmune diseases) in a subject. Treatment of a subject with a proliferative disease using a compound or composition of the invention may inhibit the aberrant activity of cyclin-dependent kinase 7 (CDK7), and therefore, induce cellular apoptosis and/or inhibit transcription in the subject.

"On Water" Direct C-3 Arylation of 2H-Pyrazolo[3,4-b]pyridines

An "on water" palladium-catalyzed direct (hetero)arylation of 2H-pyrazolo[3,4-b]pyridines has been developed. The reactions proceeds smoothly with at low catalytic loading at low temperature providing the C3 (hetero)arylated products in good to excellent isolated yields. Free NH 3-arylated 7-azaindazoles were also prepared by simple cleavage of the N-protected groups.

PYRIMIDINE AND TRIAZINE DERIVATIVES AND THEIR USE AS AXL INHIBITORS

Compounds of the general formula(I): (I) processes for the preparation of these compounds, compositions containing these compounds, and the uses of these compounds.

Design, synthesis and evaluation of 7-azaindazolyl-indolyl-maleimides as glycogen synthase kinase-3β (GSK-3β) inhibitors

A series of 7-azaindazolyl-indolyl-maleimides were designed, synthesized and evaluated for their GSK-3β inhibitory activity. Most compounds exhibited potent activity against GSK-3β. Among them, compounds 17a, 17b, 17g, 17i, 29a and 30 significantly reduced Aβ-induced Tau hyperphosphorylation, showin;g the inhibition of GSK-3β at the cell level. Preliminary structure-activity relationships were discussed based on the experimental data obtained.

INHIBITORS OF INFLUENZA VIRUSES REPLICATION

Methods of inhibiting the replication of influenza viruses in a biological sample or patient, of reducing the amount of influenza viruses in a biological sample or patient, and of treating influenza in a patient, comprises administering to said biological sample or patient an effective amount of a compound represented by Structural Formula (I): or a pharmaceutically acceptable salt thereof, wherein the values of Structural Formula (I) are as described herein. A compound is represented by Structural Formula (I) or a pharmaceutically acceptable salt thereof, wherein the values of Structural Formula (I) are as described herein. A pharmaceutical composition comprises an effective amount of such a compound or pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier, adjuvant or vehicle.

Synthesis and biological evaluation of imidazo[4,5-b]pyridine and 4-heteroaryl-pyrimidine derivatives as anti-cancer agents

A series of N-phenyl-imidazo[4,5-b]pyridin-2-amines, 4-indazolyl-N- phenylpyrimidin-2-amines and N-phenyl-4-pyrazolo[3,4-b]pyridin-pyrimidin-2- amines have been synthesized. Their anti-proliferative activities were tested in HCT-116 human colon carcinoma and MCF-7 breast carcinoma cell lines. Many exhibited potent anti-proliferative and CDK9 inhibitory activities. A lead compound 18b demonstrated the ability to reduce the level of Mcl-1 anti-apoptotic protein, to activate caspase 3/7 and induce cancer cell apoptosis.

INDAZOLEPROPIONIC ACID AMIDE COMPOUND

Disclosed is a compound which is useful in preventing and treating cardiac arrhythmia such as atrial fibrillation. A compound represented by formula (1) or a pharmaceutically acceptable salt of the same. In formula (1), ring X represents benzene or pyridine; R1 represents an optionally substituted alkyl group; R2 represents an optionally substituted aryl group, an optionally substituted heterocyclic group, an optionally substituted arylalkyl group or an optionally substituted heterocyclic group-substituted alkyl group; R3, R4, R5, R6, R7, R8 and R9 represent each hydrogen or an alkyl group, provided that R3 and R5 may be bonded to each other to form, together with the carbon atom adjacent thereto, a cycloalkyl group; and m represents 0 or 1.