89694-10-0

Basic information

• Product Name: 2-Methoxy-5-nitro-3-picoline
• Synonyms: 2-METHOXY-5-NITRO-3-PICOLINE;Pyridine,2-Methoxy-3-Methyl-5-nitro-
• CAS NO: 89694-10-0
• Molecular Formula: C7H8N2O3
• Molecular Weight: 168.15
• EINECS: -0
• Product Categories: Pyridine
• Mol File: 89694-10-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 279.7 °C at 760 mmHg
• Flash Point: 123 °C
• Appearance: off-white solid
• Density: 1.247 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -0.34±0.20(Predicted)
• CAS DataBase Reference: 2-Methoxy-5-nitro-3-picoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methoxy-5-nitro-3-picoline(89694-10-0)
• EPA Substance Registry System: 2-Methoxy-5-nitro-3-picoline(89694-10-0)

Safety Data

• Hazardous Substances Data: 89694-10-0(Hazardous Substances Data)

Usage

Description

2-Methoxy-5-nitro-3-picoline, also known as 2-Methoxy-3-methyl-5-nitropyridine, is a heterocyclic organic compound with a molecular formula of C6H6N2O3. It features a pyridine ring with a nitro group at the 5-position, a methoxy group at the 2-position, and a methyl group at the 3-position. 2-Methoxy-5-nitro-3-picoline is known for its potential applications in the pharmaceutical industry.

Uses

Used in Pharmaceutical Industry:
2-Methoxy-5-nitro-3-picoline is used as a key intermediate in the synthesis of heteroaromatic cyanoindoline derivatives, which are known as NIK inhibitors. These inhibitors play a crucial role in the regulation of the NF-κB signaling pathway, which is involved in various cellular processes, including inflammation, immune response, and cell survival. By targeting NIK, these inhibitors can potentially be used in the development of therapeutic agents for the treatment of inflammatory and autoimmune diseases, as well as cancer.

Upstream product

• 2369-18-8 2-fluoro-3-methylpyridine 
• 22280-56-4 2-chloro-3-methyl-5-nitropyridine 
• 124-41-4 sodium methylate 
• 19230-59-2 2-methoxy-3-methylpyridine 

Downstream Products

• 867012-70-2 6-methoxy-5-methylpyridin-3-amine 
• 57179-69-8 6-Hydroxy-3-nitro-2,5-lutidin 
• 57179-69-8 3,6-dimethyl-5-nitropyridin-2-one 
• 1188407-45-5 (S)-4-(1-cyclopropyl-2-methoxyethyl)-6-(6-(difluoromethoxy)-2,5-dimethylpyridin-3-ylamino)-5-oxo-4,5-dihydropyrazine-2-carbonitrile 
• 1188407-20-6 2-(6-methoxy-5-methyl-3-nitropyridin-2-yl)acetic acid 

Relevant articles and documents

Design, synthesis and structure-activity-relationship of 1,5-tetrahydronaphthyridines as CETP inhibitors

This Letter describes the discovery and SAR optimization of 1,5-tetrahydronaphthyridines, a new class of potent CETP inhibitors. The effort led to the identification of 21b and 21d with in vitro human plasma CETP inhibitory activity in the nanomolar range (IC50 = 23 and 22 nM, respectively). Both 21b and 21d exhibited robust HDL-c increase in hCETP/hApoA1 dual heterozygous mice model.

A strategy to minimize reactive metabolite formation: Discovery of (S)-4-(1-cyclopropyl-2-methoxyethyl)-6-[6-(difluoromethoxy)-2, 5-dimethylpyridin-3-ylamino]-5-oxo-4,5-dihydropyrazine-2-carbonitrile as a potent, orally bioavailable corticotropin-releasing factor-1 receptor antagonist

Detailed metabolic characterization of 8, an earlier lead pyrazinone-based corticotropin-releasing factor-1 (CRF1) receptor antagonist, revealed that this compound formed significant levels of reactive metabolites, as measured by in vivo and in vitro biotransformation studies. This was of particular concern due to the body of evidence suggesting that reactive metabolites may be involved in idiosyncratic drug reactions. Further optimization of the structure-activity relationships and in vivo properties of pyrazinone-based CRF1 receptor antagonists and studies to assess the formation of reactive metabolites led to the discovery of 19e, a high affinity CRF1 receptor antagonist (IC50= 0.86 nM) wherein GSH adducts were estimated to be only 0.1% of the total amount of drug-related material excreted through bile and urine, indicating low levels of reactive metabolite formation in vivo. Anovel 6-(difluoromethoxy)-2,5-dimethylpyridin-3- amine group in 19e contributed to the potency and improved in vivo properties of this compound and related analogues. 19e had excellent pharmacokinetic properties in rats and dogs and showed efficacy in the defensive withdrawal model of anxiety in rats. The lowest efficacious dose was 1.8 mg/kg. The results of a two-week rat safety study with 19e indicated that this compound was well-tolerated.