7464-14-4

Usage

Uses

Used in Chemical Synthesis:
2-Hydroxy-5-methyl-3-nitropyridine is used as an intermediate in the synthesis of various chemical compounds. It can be converted into 2-chloro-5-methyl-3-nitropyridine through chlorination using thionyl chloride, which is a common reagent in organic chemistry.
Used in Pharmaceutical Industry:
2-Hydroxy-5-methyl-3-nitropyridine is used as a building block in the preparation of proteasome inhibitors containing the 5-methylpyridin-2(1H)-one moiety. Proteasome inhibitors are a class of drugs that target the proteasome, an enzyme complex responsible for the degradation of proteins in cells. These inhibitors have potential applications in the treatment of various diseases, including cancer and inflammatory disorders, by modulating the activity of the proteasome and affecting the balance of proteins within cells.

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 
• 1003-68-5 5-methyl-pyridin-2-ol 
• 1603-41-4 (5-methyl-pyridin-2-yl)amine 

Downstream Products

• 52334-51-7 3-amino-5-methylpyridin-2-ol 
• 23056-40-8 2-chloro-5-methyl-3-nitro-pyridine 
• 23056-46-4 2-bromo-5-methyl-3-nitropyridine 
• 1443995-60-5 C₂₁H₂₆N₄O₅ 
• 1443995-66-1 C₂₁H₂₇N₅O₃ 
• 1443995-27-4 C₁₆H₁₈N₄O₃ 
• 1408054-37-4 C₁₆H₁₉N₅O 
• 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 
• 1353547-75-7 (E)-N-(2-methoxy-5-(((2,4,6-trimethoxystyryl)sulfonyl)methyl)pyridin-3-yl)methanesulfonamide 
• 1353547-76-8 (E)-ethyl 2-((2-methoxy-5-(((2,4,6-trimethoxystyryl)sulfonyl)methyl)pyridin-3-yl)amino)acetate 
• 1353547-77-9 (E)-2-((2-methoxy-5-(((2,4,6-trimethoxystyryl)sulfonyl)methyl)pyridin-3-yl)amino)acetic acid 
• 1353547-78-0 (E)-N-ethyl-N-(2-methoxy-5-(((2,4,6-trimethoxystyryl)sulfonyl)methyl)pyridin-3-yl)acetamide 

Relevant academic research and scientific papers

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.

Synthesis and evaluation of 8-amino-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one derivatives as glycogen synthase kinase-3 (GSK-3) inhibitors

New potent glycogen synthase kinase-3 (GSK-3) inhibitors, 8-amino-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one derivatives, were designed by modeling, synthesized and evaluated in vitro. Compound 17c showed good potency in enzyme and cell-based assays (IC50 = 111 nM, EC50 = 1.78 μM). Moreover, it has demonstrated desirable water solubility, PK profile, and moderate brain penetration.

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.

Synthesis and pharmacological evaluation of a second generation of pyridothiadiazine 1,1-dioxides acting as AMPA potentiators

Taking into account structure-activity relationships obtained with our previous series, new diversely substituted 1,2,4-pyridothiadiazine 1,1-dioxides were designed to obtain novel AMPA potentiators. The aim of this work was focused on the improvement of lipophilicity, which is well known as a critical parameter to obtain in vivo active central nervous system agents. For this purpose, two positions on the pyridine ring were privileged to insert selected groups. Among the synthesized compounds emerged 7-chloro-4-ethyl-3,4-dihydro-2H-pyrido[2,3-e]-[1,2,4]-thiadiazine 1,1-dioxide (12d), which was evaluated in two memory tests in Wistar rats and showed cognition enhancing effects after intraperitoneal injection at doses as low as 0.3 mg/kg.

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.