123631-83-4

Basic information

• Product Name: 4-Hydroxy-2,3-dimethoxypyridine
• Synonyms: 4-Hydroxy-2,3-dimethoxypyridine;2,3-Dimethoxy-pyridin-4-ol;4-Pyridinol, 2,3-dimethoxy-;4-Hydroxy-2,3-Dimethoxypyridine(WX649117)
• CAS NO: 123631-83-4
• Molecular Formula: C7H9NO3
• Molecular Weight: 155.15
• Mol File: 123631-83-4.mol

Chemical Properties

• Boiling Point: 358.4±37.0 °C(Predicted)
• Appearance: /
• Density: 1.201±0.06 g/cm3(Predicted)
• PKA: 4.89±0.23(Predicted)
• CAS DataBase Reference: 4-Hydroxy-2,3-dimethoxypyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxy-2,3-dimethoxypyridine(123631-83-4)
• EPA Substance Registry System: 4-Hydroxy-2,3-dimethoxypyridine(123631-83-4)

Safety Data

• Hazardous Substances Data: 123631-83-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Hydroxy-2,3-dimethoxypyridine is used as a key intermediate in the synthesis of various pharmaceuticals for its potential biological activities. Its unique structure allows for the development of new drugs with specific therapeutic targets.
Used in Agrochemical Industry:
In the agrochemical sector, 4-Hydroxy-2,3-dimethoxypyridine is utilized as a precursor in the production of agrochemicals, contributing to the development of effective pesticides and other agricultural chemicals.
Used in Antioxidant and Anti-Inflammatory Drug Development:
4-Hydroxy-2,3-dimethoxypyridine is studied for its antioxidant and anti-inflammatory properties, making it a potential candidate for the development of new drugs targeting oxidative stress and inflammation-related conditions.
Used in Medicinal Chemistry Research:
4-Hydroxy-2,3-dimethoxypyridine is employed in medicinal chemistry research to explore its potential applications in drug discovery and development, given its unique structural features and biological activities.

Upstream product

• 52605-97-7 2,3-dimethoxypyridine 
• 109-09-1 2-chloropyridine 
• 52605-96-6 2-chloro-3-methoxypyridine 
• 6636-78-8 2-chloro-3-hydroxypyridine 
• 13472-83-8 2-methoxy-3-hydroxypyridine 
• 108082-72-0 2-chloro-3-benzyloxypyridine 

Relevant articles and documents

Synthesis and Antineoplastic Evaluation of Mitochondrial Complex II (Succinate Dehydrogenase) Inhibitors Derived from Atpenin A5

Mitochondrial complex II (CII) is an emerging target for numerous human diseases. Sixteen analogues of the CII inhibitor natural product atpenin A5 were prepared to evaluate the structure–activity relationship of the C5 pyridine side chain. The side chain ketone moiety was determined to be pharmacophoric, engendering a bioactive conformation. One analogue, 1-(2,4-dihydroxy-5,6-dimethoxypyridin-3-yl)hexan-1-one (16 c), was found to have a CII IC50 value of 64 nm, to retain selectivity for CII over mitochondrial complex I (>156-fold), and to possess a ligand-lipophilicity efficiency (LLE) of 5.62, desirable metrics for a lead compound. This derivative and other highly potent CII inhibitors show potent and selective anti-proliferative activity in multiple human prostate cancer cell lines under both normoxia and hypoxia, acting to inhibit mitochondrial electron transport.

METHOD OF TREATING CANCER WITH ATPENIN A5 DERVIATIVES

The present invention includes molecules, composition, and methods for making and using a molecule having the formula (I), wherein R' is selected from H, methoxy, or methoxymethyl; X is selected from H, OH, methoxy, or methoxymethyl or O- methoxymethyl; Y is O; and R" is selected from H, OH, 2-furan, ethyl, propyl, pentyl, hexyl, heptyl, octyl, nonly, decyl, or dodecyl, that are saturated or unsaturated.

Total synthesis of 4-epi-atpenin A5 as a potent nematode complex II inhibitor

It is clear that atpenins and their analogs are useful chemical tools for elucidation of complex II functionality and that they could act as lead compounds for the development of novel helminth complex II-specific inhibitors. Recently, we discovered 4-epi

Synthetic atpenin analogs: Potent mitochondrial inhibitors of mammalian and fungal succinate-ubiquinone oxidoreductase

Atpenins and harzianopyridone represent a unique class of penta-substituted pyridine-based natural products that are potent inhibitors of complex II (succinate-ubiquinone oxidoreductase) in the mitochondrial respiratory chain. These compounds block electron transfer in oxidative phosphorylation by inhibiting oxidation of succinate to fumarate and the coupled reduction of ubiquinone to ubiquinol. From our investigations of complex II inhibitors as potential agricultural fungicides, we report here on the synthesis and complex II inhibition for a series of synthetic atpenin analogs against both mammalian and fungal forms of the enzyme. Synthetic atpenin 2e provided optimum mammalian and fungal inhibition with slightly higher potency than natural occurring atpenin A5.

Titanium(II)-mediated cyclizations of (silyloxy)enynes: A total synthesis of (-)-7-demethylpiericidin A1

A concise total synthesis of 7-demethylpiericidin A1 has been completed. The synthesis features a titanium(II)-mediated cyclization of a (silyloxy)enyne as the key step and proceeds in nine steps from tiglic aldehyde. Copyright

Total Synthesis of (+/-)-Atpenin B. An Original "Clockwise" Functionalization of 2-Chloropyridine

(-)-Atpenin B (1) is an antibiotic produced by Penicillim sp.FO-125.The first synthesis of 2,4-dihydroxy-5,6-dimethoxy-3-((2RS,4RS)-2,4-dimethyl-1-oxohexyl)pyridine (atpenin B) (16) is reported.This molecule, which exhibits a pentasubstituted pyridine structure, was prepared from 2-chloropyridine in 13 steps, by metalating and then functionalizing, one after another, all the remaining positions of the pyridine ring.The methodology involves four metalation steps (including metalation of 2,3-dimethoxypyridine and pyridyl N,N-diisopropylcarbamates), one halogen-scrambling step, and one bromine-lithium exchange step.