54221-95-3

Basic information

• Product Name: 2-ACETYLAMINO-ISONICOTINIC ACID
• Synonyms: 2-ACETYLAMINO-ISONICOTINIC ACID;2-AECTAMIDO-4-PYRIDINECARBOXYLIC ACID;2-ACETAMIDOISONICOTINIC ACID;2-(Acetylamino)isonicotinic acid 97%;2-Acetamido-4-pyridinecarboxylic acid;Zinc02559887;2-acetaMidopyridine-4-carboxylic acid;2-(Acetylamino)pyridine-4-carboxylic acid
• CAS NO: 54221-95-3
• Molecular Formula: C₈H₈N₂O₃
• Molecular Weight: 180.16
• Product Categories: Amines;blocks;Carboxes;Pyridines
• Mol File: 54221-95-3.mol
• Article Data: 20

Chemical Properties

• Melting Point: 286-290
• Boiling Point: 585.3 °C at 760 mmHg
• Flash Point: 307.8 °C
• Appearance: /
• Density: 1.404 g/cm³
• Vapor Pressure: 1.52E-14mmHg at 25°C
• Refractive Index: 1.628
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 1.74±0.10(Predicted)
• CAS DataBase Reference: 2-ACETYLAMINO-ISONICOTINIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ACETYLAMINO-ISONICOTINIC ACID(54221-95-3)
• EPA Substance Registry System: 2-ACETYLAMINO-ISONICOTINIC ACID(54221-95-3)

Safety Data

• Hazard Codes: Xi
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 54221-95-3(Hazardous Substances Data)

Usage

Description

2-Acetylaminoisonicotinic Acid, also known as AIA, is an organic compound with the molecular formula C8H8N2O3. It is a derivative of isonicotinic acid, featuring an acetylamino group at the 2nd position. 2-ACETYLAMINO-ISONICOTINIC ACID serves as a key intermediate in the synthesis of various pharmaceuticals and has potential applications in the medical field due to its unique chemical structure and properties.

Uses

Used in Pharmaceutical Industry:
2-Acetylaminoisonicotinic Acid is used as a reactant for the preparation of nicotinic acid analogues, which are potent hypoxia-inducible factor (HIF)-1α inhibitors. These analogues play a crucial role in the development of drugs targeting various diseases, including anemia, cancer, and other conditions related to the HIF-1α pathway. By inhibiting HIF-1α, these analogues can help regulate cellular responses to hypoxia and potentially improve treatment outcomes for patients suffering from these diseases.

InChI:InChI=1/C8H8N2O3/c1-5(11)10-7-4-6(8(12)13)2-3-9-7/h2-4H,1H3,(H,12,13)(H,9,10,11)

Upstream product

• 6937-03-7 methyl 2-aminoisonicotinate 
• 75-36-5 acetyl chloride 
• 695-34-1 2-Amino-4-methylpyridine 
• 108-24-7 acetic anhydride 
• 13362-28-2 2-aminoisonicotinic acid 
• 5327-32-2 2-acetylamino-4-methylpyridine 

Downstream Products

• 13362-30-6 2-amino-4-ethoxycarbonyl-pyridine 
• 908380-97-2 N-{4-[5-(4-fluoro-phenyl)-3-methyl-2-methylsulfinyl-3H-imidazol-4-yl]-pyridin-2-yl}-acetamide 
• 452056-88-1 C₁₇H₁₅FN₄OS 
• 6937-03-7 methyl 2-aminoisonicotinate 
• 14436-36-3 2-(acetylamido)isonicotinamide 
• 98953-21-0 methyl 2-acetamidoisonicotinate 
• 13538-42-6 2-amino-isonicotinamide 
• 84487-09-2 2-amino-5-nitropyridine-4-carboxylic acid 
• 452056-93-8 N-{4-[4-(4-fluorophenyl)-1-methyl-2-methylsulfanyl-1H-imidazol-5-yl]pyridin-2-yl}acetamide 

Relevant articles and documents

Discovery of 2-(cyclopropanecarboxamido)-N-(5-((1-(4-fluorobenzyl)piperidin-4-yl)methoxy)pyridin-3-yl)isonicotinamide as a potent dual AChE/GSK3β inhibitor for the treatment of Alzheimer's disease: Significantly increasing the level of acetylcholine in the brain without affecting that in intestine

Acetylcholinesterase (AChE) inhibitors are currently the first-line drugs approved by the FDA for the treatment of Alzheimer's disease (AD). However, a short effective-window limits their therapeutic benefits. Clinical studies have confirmed that the combination of AChE inhibitors and neuroprotective agents exhibits better anti-AD effects. We have previously reported that the dual AChE/GSK3β (Glycogen synthase kinase 3β) modulators have both neuroprotective effects and cognitive impairment-improvement effects. In this study, we characterized a new backbone of the AChE/GSK3β inhibitor 11c. It was identified as a highly potent AChE inhibitor and was found superior to donepezil, the first-line drug for the treatment of AD. In vivo studies confirmed that 11c significantly inhibited the activity of AChE in the brain but had little effect on the activity of AChE in the intestine. This advantage of 11c was expected to reduce the peripheral side effects caused by donepezil. Furthermore, biomarker studies have shown that 11c also improved the levels of acetylcholine and synaptophysin in the brain and exhibited neuroprotective effects. Preliminary in vivo and in vitro research results underline the exciting potential of compound 11c in the treatment of AD.

Discovery of N-{4-[5-(4-Fluorophenyl)-3-methyl-2-methylsulfanyl-3H-imidazol-4-yl]-pyridin-2-yl}-acetamide (CBS-3595), a Dual p38α MAPK/PDE-4 Inhibitor with Activity against TNFα-Related Diseases

The anti-inflammatory potential of p38 mitogen-activated protein kinase (MAPK) inhibitors was coincidentally expanded to a dual inhibition of p38α MAPK and phosphodiesterase 4 (PDE4), and the potential benefits arising from the blockage of both inflammation-related enzymes were thoroughly investigated. The most promising compound, CBS-3595 (1), was successively evaluated in in vitro experiments as well as in ex vivo and in vivo preclinical studies after administration of 1 to rodents, dogs, and monkeys. The resulting data clearly indicated a potent suppression of tumor necrosis factor alpha release. For reconfirming the findings of the animal studies when administering 1 to healthy human volunteers, a phase I clinical trial was conducted. Apart from further information regarding the pharmacokinetic and pharmacodynamic characteristics of 1, it was demonstrated that dual inhibition of p38α MAPK and PDE4 is able to synergistically attenuate the excessive anti-inflammatory response.

DEUTERIUM-ENRICHED HETEROCYCLIC COMPOUNDS AS KINASE INHIBITORS

The present invention provides deuterium-enriched heteroaryl-containing urea compounds (I) and use of the same for treating conditions mediated by protein kinase such as