1196156-42-9

Basic information

• Product Name: Methyl 1H-pyrazolo[3,4-b]pyridine-5-carboxylate
• Synonyms: Methyl 1H-pyrazolo[3,4-b]pyridine-5-carboxylate;1H-Pyrazolo[3,4-b]pyridine-5-carboxylic acid, Methyl ester
• CAS NO: 1196156-42-9
• Molecular Formula: C₈H₇N₃O₂
• Molecular Weight: 177.16008
• Mol File: 1196156-42-9.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: Methyl 1H-pyrazolo[3,4-b]pyridine-5-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 1H-pyrazolo[3,4-b]pyridine-5-carboxylate(1196156-42-9)
• EPA Substance Registry System: Methyl 1H-pyrazolo[3,4-b]pyridine-5-carboxylate(1196156-42-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 1196156-42-9(Hazardous Substances Data)

Usage

General Description

Methyl 1H-pyrazolo[3,4-b]pyridine-5-carboxylate is a chemical compound with the molecular formula C9H7N3O2. It belongs to the pyrazolo[3,4-b]pyridine-5-carboxylate family and is commonly used in organic synthesis and pharmaceutical research. Methyl 1H-pyrazolo[3,4-b]pyridine-5-carboxylate is known for its potential therapeutic properties and is being studied for its potential applications in drug discovery. It is commonly used as a building block in the synthesis of various pharmaceutical compounds, and its unique structure and properties make it a valuable tool for medicinal chemistry research. Additionally, it is important to handle this chemical compound with caution and adhere to proper safety protocols due to its potential health hazards.

Upstream product

• 67-56-1 methanol 
• 875781-17-2 5-bromo-7-azaindazole 
• 201230-82-2 carbon monoxide 
• 952182-02-4 1H-pyrazolo[3,4-b] pyridine-5-carboxylic acid 
• 875781-15-0 5-bromo-2-fluoro-3-pyridinecarboxaldehyde 
• 1234616-67-1 1H-pyrazolo[3,4-b]pyridine-5-carbonitrile 

Downstream Products

• 1581701-34-9 N-(2-methyl-5-((4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)carbamoyl)phenyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxamide 
• 952182-02-4 1H-pyrazolo[3,4-b] pyridine-5-carboxylic acid 

Relevant articles and documents

Zinc Acetate-Promoted Buchwald-Hartwig Couplings of Heteroaromatic Amines

Zinc salts have been shown to promote the Buchwald-Hartwig coupling of azaindoles and azaindazoles with heteroaryl chlorides to provide the corresponding 1-aryl-1H-azaindoles and 1-aryl-1H-azaindazoles. The substrate scope and mechanistic aspects of this reaction were explored.

Reversible Inhibitors Arrest ClpP in a Defined Conformational State that Can Be Revoked by ClpX Association

Caseinolytic protease P (ClpP) is an important regulator of Staphylococcus aureus pathogenesis. A high-throughput screening for inhibitors of ClpP peptidase activity led to the identification of the first non-covalent binder for this enzyme class. Co-crystallization of the small molecule with S. aureus ClpP revealed a novel binding mode: Because of the rotation of the conserved residue proline 125, ClpP is locked in a defined conformational state, which results in distortion of the catalytic triad and inhibition of the peptidase activity. Based on these structural insights, the molecule was optimized by rational design and virtual screening, resulting in derivatives exceeding the potency of previous ClpP inhibitors. Strikingly, the conformational lock is overturned by binding of ClpX, an associated chaperone that enables proteolysis by substrate unfolding in the ClpXP complex. Thus, regulation of inhibitor binding by associated chaperones is an unexpected mechanism important for ClpP drug development.

Identification and optimization of new dual inhibitors of B-Raf and epidermal growth factor receptor kinases for overcoming resistance against vemurafenib

Epidermal growth factor receptor (EGFR) amplification has been demonstrated to be critical for the inherent and/or acquired resistance against current B-RafV600E inhibitor therapy for melanoma and colorectal cancer patients. We describe the discovery and structure-activity relationship study of a series of 1H-pyrazolo[3,4-b]pyridine-5-carboxamide analogues as novel dual inhibitors of EGFR and B-RafV600E mutant. One of the most promising compounds, 6a, potently inhibited both of the kinases with IC50 values of 8.0 and 51 nM, respectively. The compound also strongly suppressed the proliferation of a panel of intrinsic and acquired resistant melanoma and/or colorectal cancer cells harboring overexpressed EGFR with submicromolar IC 50 values. Further mechanism investigation revealed that 6a could sustainably inhibit the activation of the MAPK path way in the resistant SK-MEL-28 PR30 melanoma cancer cells and WiDr colorectal cancer cells with EGFR amplification. Our results support the hypothesis that the EGFR/B-Raf V600E dual inhibition might be a tractable strategy to overcome the intrinsic and acquired resistance of melanoma and/or colorectal cancers against the current B-RafV600E inhibitor therapy.