36953-37-4

Basic information

• Product Name: 4-BROMOPYRIDIN-2-OL
• Synonyms: 4-Iodoopyridin-2(1H)-one;4-BROMO-2-PYRIDINOL;4-BROMO-2-HYDROXYPYRIDINE;4-BROMOPYRIDIN-2-OL;4-Iodo-1H-pyridin-2-one;2-HYDROXY-4-BROMOPYRIDINE;4-IODOPYRIDIN-2(1H)-ONE;4-Iodo-1H-pyridin-2-one 97%
• CAS NO: 36953-37-4
• Molecular Formula: C₅H₄BrNO
• Molecular Weight: 174
• Product Categories: Pyridine Series;pharmacetical;Halides;Pyridines;Pyridine;Heterocycle-Pyridine series
• Mol File: 36953-37-4.mol

Chemical Properties

• Melting Point: 186 °C
• Boiling Point: 305.9 °C at 760 mmHg
• Flash Point: 138.8 °C
• Appearance: White/Crystalline Powder
• Density: 1.776 g/cm³
• Vapor Pressure: 0.418mmHg at 25°C
• Refractive Index: 1.543
• Storage Temp.: Room temperature.
• PKA: 10.54±0.10(Predicted)
• CAS DataBase Reference: 4-BROMOPYRIDIN-2-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BROMOPYRIDIN-2-OL(36953-37-4)
• EPA Substance Registry System: 4-BROMOPYRIDIN-2-OL(36953-37-4)

Safety Data

• Statements: 36/38
• Safety Statements: 36
• Hazardous Substances Data: 36953-37-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-BROMOPYRIDIN-2-OL is used as a reagent for the synthesis of trans-3,4’-bispyridinylethylenes. These compounds are known to act as inhibitors of protein kinase B (PKB), which plays a crucial role in various cellular processes, including cell survival, growth, and apoptosis. By inhibiting PKB, these compounds can potentially be used in the treatment of cancer, as they may help to prevent the uncontrolled growth and proliferation of cancer cells.
Additionally, 4-BROMOPYRIDIN-2-OL can be utilized in the development of other bioactive molecules and pharmaceutical agents, given its unique structural features and reactivity. Its potential applications in drug discovery and design make it a valuable compound for further research and development in the pharmaceutical industry.

InChI:InChI=1/C6H6BrNO/c1-9-6-4-5(7)2-3-8-6/h2-4H,1H3

Upstream product

• 100367-39-3 4-bromo-2-methoxypyridine 
• 73583-37-6 2-chloro-4-bromopyridine 
• 1214900-01-2 2-(benzyloxy)pyridin-4-amine 
• 960298-00-4 2-(benzyloxy)-4-bromopyridine 
• 14432-12-3 4-Amino-2-chloropyridine 
• 84249-14-9 2-amino-4-bromopyridine 

Downstream Products

• 1001076-61-4 C₂₂H₂₇N₃O₂S 
• 865156-55-4 4-bromo-2-(3-methoxypropoxy)pyridine 
• 889865-56-9 4-bromo-1-(2-hydroxyethyl)pyridin-2(1H)-one 
• 1198803-37-0 2-methyl-N-[6-(2-oxo-1,2-dihydro-4-pyridinyl)-1H-indazol-4-yl]-1,3-thiazole-4-carboxamide 
• 832735-56-5 4-bromo-2-(difluoromethoxy)pyridine 
• 1237534-53-0 2-(4-bromo-pyridin-2-yloxy)-2-methyl-propionic acid methyl ester 
• 1193334-89-2 3-(4-bromo-2-oxo-2H-pyridin-1-yl)-2-methyl-propionic acid methyl ester 
• 1237534-49-4 4-bromo-1-[(S)-tetrahydro-furan-3-yl]-1H-pyridin-2-one 
• 1237534-50-7 4-bromo-2-[(S)-tetrahydro-furan-3-yloxy]-pyridine 
• 1193334-88-1 4-bromo-1-(2-hydroxy-2-methyl-propyl)-1H-pyridin-2-one 
• 1254730-45-4 C₁₄H₁₈BrNO₃ 
• 1263184-47-9 C₁₈H₁₉BrN₂O₂ 
• 960298-00-4 2-(benzyloxy)-4-bromopyridine 
• 1193334-86-9 4-bromo-1-cyclopropylpyridin-2(1H)-one 

Relevant articles and documents

NOVEL COMPOUNDS AS NADPH OXIDASE INHIBITORS

The present invention is related to new compounds, pharmaceutical composition thereof and to their use for the treatment and/or prophylaxis of disorders or conditions related to Nicotinamide adenine dinucleotide phosphate oxidase (NADPH Oxidase).

Discovery of 2-aminopyridines bearing a pyridone moiety as potent ALK inhibitors to overcome the crizotinib-resistant mutants

Despite the initial benefit demonstrated in clinical setting with ALK inhibitors, the challenging resistant mutants (F1174L, L1196M and G1202R) invariably developed. In this work, a series of 2-aminopyridine derivatives were designed and synthesized by C-5 position incorporation of a 2-pyridone moiety and bioisosteric replacement of the C-3 position linkers. Optimization of the 2-aminopyridine derivatives led to the identification of hit 18d displaying a significant growth inhibition against a variety of ALK-addicted cancer cells. Especially in the case of ALK-positive Karpas-299 cell, 18d exhibited excellent anti-proliferative potency with an IC50 value of about 40 nM. Moreover, 18d demonstrated encouraging activities against wild-type ALK (19 nM), ROS1 (2.3 nM) as well as challenging crizotinib-resistant ALKL1196M and ALKG1202R mutants with IC50 values of 45 nM and 22 nM, respectively. Additionally flow cytometric analysis indicates that 18d inhibited Karpas-299 cell viability via G1 phase arrest. Taken together, this work provided a promising ALK inhibitor to circumvent the clinical crizotinib-resistant mutants.

Concise Entries to 4-Halo-2-pyridones and 3-Bromo-4-halo-2-pyridones

Methods for the synthesis of both simple 4-halo-2-pyridones and more functionalized 3,4-di- and (3,4,5-tri)-halo-2-pyridones are described that are based on a combination of Sandmeyer and regioselective (copper-mediated) halogenation, with a 2-chloro or a 2-benzyloxy moiety serving as a masked 2-pyridone.

Asymmetric Homogeneous Hydrogenation of 2-Pyridones

An asymmetric homogeneous hydrogenation of 2(1H)-pyridones has been developed, using a ruthenium complex bearing two chiral N-heterocyclic carbene (NHC) ligands. To the best of our knowledge, the presented reaction is the first example of a homogeneous asymmetric conversion of 2-pyridones into the corresponding enantioenriched 2-piperidones.

Intrinsic electrophilicity of the 4-methylsulfonyl-2-pyridone scaffold in glucokinase activators: Role of glutathione-S-transferases and in vivo quantitation of a glutathione conjugate in rats

Previous studies on the in vitro metabolism of 4-alkylsulfonyl-2-pyridone- based glucokinase activators revealed a facile, non-enzymatic displacement of the 4-alkylsulfonyl group by glutathione. In the present studies, a role for glutathione-S-transferases (GST) as catalysts in the desulfonylation reaction was demonstrated using a combination of human liver microsomes, human liver cytosol and human GSTs. The identification of a glutathione conjugate in circulation following intravenous administration of a candidate 4-methylsulfonyl-2-pyridone to rats confirmed the relevance of the in vitro findings.

MODULATORS OF CFTR

Compounds of the present invention, and pharmaceutically acceptable compositions thereof, are useful as modulators of ATP-Binding Cassette ("ABC") transporters or fragments thereof, including Cystic Fibrosis Transmembrane Conductance Regulator ("CFTR"). The present invention also relates to methods of treating CFTR mediated diseases using compounds of the present invention.