7464-14-4

Basic information

• Product Name: 2-Hydroxy-5-methyl-3-nitropyridine
• Synonyms: 2-HYDROXY-5-METHYL-3-NITROPYRIDINE;2-HYDROXY-3-NITRO-5-METHYLPYRIDINE;2-HYDROXY-3-NITRO-5-PICOLINE;5-METHYL-3-NITRO-2(1H)-PYRIDINONE;3-(NITRO)-5-METHYLPYRIDIN-2-OL;2-Hydroxy-5-methyl-3-nitropyridine 98%;5-Methyl-3-nitropyridin-2-ol;2-HYDROXY-3-NITRO-5-PICOLINE (2-HYDROXY-5-METHYL-3-NITROPYRIDINE)
• CAS NO: 7464-14-4
• Molecular Formula: C₆H₆N₂O₃
• Molecular Weight: 154.12
• Product Categories: compounds of pyridine;blocks;NitroCompounds;Pyridines;Pyridine;C6;Heterocyclic Building Blocks
• Mol File: 7464-14-4.mol
• Article Data: 5

Chemical Properties

• Melting Point: 179 °C (dec.)(lit.)
• Boiling Point: 353.3 °C at 760 mmHg
• Flash Point: 167.4 °C
• Appearance: /
• Density: 1.24 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.63E-05mmHg at 25°C
• Refractive Index: 1.567
• Storage Temp.: 2-8°C
• Solubility: soluble in Dimethylformamide
• CAS DataBase Reference: 2-Hydroxy-5-methyl-3-nitropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Hydroxy-5-methyl-3-nitropyridine(7464-14-4)
• EPA Substance Registry System: 2-Hydroxy-5-methyl-3-nitropyridine(7464-14-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 7464-14-4(Hazardous Substances Data)

Usage

Uses

2-Hydroxy-5-methyl-3-nitropyridine may be used in the preparation of 2-chloro-5-methyl-3-nitropyridine via chlorination, using thionyl chloride. It may also be used is preparing proteasome inhibitors containing 5-methylpyridin-2(1H)-one moiety.

InChI:InChI=1/C6H6N2O3/c1-4-2-5(8(10)11)6(9)7-3-4/h2-3H,1H3,(H,7,9)

Upstream product

• 123-38-6 propionaldehyde 
• 17758-33-7 3-methyl-5-nitro-4(3H)-pyrimidinone 
• 1603-41-4 (5-methyl-pyridin-2-yl)amine 
• 1003-68-5 5-methyl-pyridin-2-ol 

Downstream Products

• 52334-51-7 3-amino-5-methylpyridin-2-ol 
• 23056-40-8 2-chloro-5-methyl-3-nitro-pyridine 
• 33252-62-9 2-methoxy-5-methyl-3-nitropyridine 
• 179677-17-9 2-methoxy-5-methylpyridin-3-ylamine 
• 179677-19-1 N-(4-Iodo-5-methyl-2-oxo-1,2-dihydro-pyridin-3-yl)-2,2-dimethyl-propionamide 
• 6960-20-9 3-methyl-5-nitropyridine 
• 2047-49-6 5-nitropyridine-3-carboxylic acid 
• 21901-25-7 3-nitro-5-methyl-2-hydrazine-pyridine 
• 23056-46-4 2-bromo-5-methyl-3-nitropyridine 
• 23945-84-8 6-chloro-5-nitro-nicotinoyl chloride 
• 7477-10-3 6-chloro-5-nitronicotinic acid 
• 1353547-72-4 (E)-2-methoxy-3-nitro-5-(((2,4,6-trimethoxystyryl)sulfonyl)methyl)pyridine 
• 1353547-73-5 (E)-2-methoxy-5-(((2,4,6-trimethoxystyryl)sulfonyl)methyl)pyridin-3-amine 
• 1353547-74-6 (E)-N-(2-methoxy-5-(((2,4,6-trimethoxystyryl)sulfonyl)methyl)pyridin-3-yl)acetamide 

Relevant articles and documents

Computer-aided discovery of aminopyridines as novel JAK2 inhibitors

The Janus kinase 2 (JAK2)-mediated signaling pathway plays an important role in controlling cell survival, proliferation, and differentiation. In recent years, genetic, biological, and physiological evidence has established JAK2 inhibitors as effective chemotherapeutic agents for the treatment of many different cancers. For this reason, we sought to identify novel small molecule inhibitors of JAK2. Using Surflex-Dock software, we tested 3010 compounds with known chemical structures in silico for their ability to interact with the JAK2 ATP-binding pocket. We selected the 10 highest-scoring compounds and tested their abilities to inhibit JAK2 activity in vitro. Compound 1a (ethyl 1-(5-((3-methoxyphenyl)carbamoyl)-3-nitropyridin-2-yl)piperidine-4-carboxylate) was identified. Optimization of 1a using docking studies led to the discovery of compounds 1b and 1d, potent JAK2 inhibitors. Furthermore, as V-shaped kinase inhibitors can curve around the protein backbone and access deep into the pocket, we developed a new series of compounds with a non-linear sulfonamide bond. Nine compounds were prepared and evaluated for JAK2 inhibitory effects. Compounds 7e (IC50 = 6.9 μM) and 7h (IC50 = 12.2 μM) showed better JAK2 inhibition, validating our design approach. This study successfully applied virtual screening for hit discovery, and a docking study for hit optimization. In addition, a novel approach to drug discovery, combining structure- and shape-based drug design, facilitated the design of more potent JAK2 inhibitors. The methods provide a guide for future development of inhibitors targeting JAK2 and other kinases.

THE NITROPYRIDINYL ETHYLENEIMINE COMPOUND, THE PHARMACEUTICAL COMPOSITION CONTAINING IT, THE PREPARATION METHOD AND USE THEREOF

The present invention discloses a nitropyridinyl ethyleneimine compound as shown in the formula I and a preparation method of the same, as well as use of the compound in manufacture of a prodrug and in manufacture of a drug for treating a tumor.

Novel ring transformation of nitropyrimidinone; synthetic equivalent of α-nitroformylacetic acid

3-Methyl-5-nitropyrimidin-4(3H)-one reacts with ketones in the presence of ammonium salts to afford disubstituted pyrimidines and disubstituted 3-nitro-2-pyridones in a novel ring transformation reaction; nitropyrimidinone behaves as an activated diformylamine in the former case, and as a synthetic equivalent of α-nitroformylacetic acid in the latter case.