1391062-95-5

Basic information

• Product Name: 2-amino-4-phenyl-6-methylnicotinonitrile N-oxide
• Synonyms: 2-amino-4-phenyl-6-methylnicotinonitrile N-oxide
• CAS NO: 1391062-95-5
• Molecular Weight: 225.25
• Mol File: 1391062-95-5.mol

Chemical Properties

• CAS DataBase Reference: 2-amino-4-phenyl-6-methylnicotinonitrile N-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-4-phenyl-6-methylnicotinonitrile N-oxide(1391062-95-5)
• EPA Substance Registry System: 2-amino-4-phenyl-6-methylnicotinonitrile N-oxide(1391062-95-5)

Safety Data

• Hazardous Substances Data: 1391062-95-5(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 18631-33-9 2-amino-6-methyl-4-phenyl-3-pyridinecarbonitrile 

Downstream Products

• 1391062-90-0 2-amino-4-phenyl-6-methylnicotinic acid N-oxide 

Relevant articles and documents

Discovering a new class of antifungal agents that selectively inhibits microbial carbonic anhydrases

Infections caused by pathogens resistant to the available antimicrobial treatments represent nowadays a threat to global public health. Recently, it has been demonstrated that carbonic anhydrases (CAs) are essential for the growth of many pathogens and their inhibition leads to growth defects. Principal drawbacks in using CA inhibitors (CAIs) as antimicrobial agents are the side effects due to the lack of selectivity toward human CA isoforms. Herein we report a new class of CAIs, which preferentially interacts with microbial CA active sites over the human ones. The mechanism of action of these inhibitors was investigated against an important fungal pathogen, Cryptococcus neoformans, revealing that they are also able to inhibit CA in microbial cells growing in vitro. At our best knowledge, this is the first report on newly designed synthetic compounds selectively targeting β-CAs and provides a proof of concept of microbial CAs suitability as an antimicrobial drug target.

2-Aminonicotinic acid 1-oxides are chemically stable inhibitors of quinolinic acid synthesis in the mammalian brain: A step toward new antiexcitotoxic agents

3-Hydroxyanthranilic acid 3,4-dioxygenase (3-HAO) is the enzyme responsible for the production of the neurotoxic tryptophan metabolite quinolinic acid (QUIN). Elevated brain levels of QUIN are observed in several neurodegenerative diseases, but pharmacological investigation on its role in the pathogenesis of these conditions is difficult because only one class of substrate-analogue 3-HAO inhibitors, with poor chemical stability, has been reported so far. Here we describe the design, synthesis, and biological evaluation of a novel class of chemically stable inhibitors based on the 2-aminonicotinic acid 1-oxide nucleus. After the preliminary in vitro evaluation of newly synthesized compounds using brain tissue homogenate, we selected the most active inhibitor and showed its ability to acutely reduce the production of QUIN in the rat brain in vivo. These findings provide a novel pharmacological tool for the study of the mechanisms underlying the onset and propagation of neurodegenerative diseases.

DERIVATIVES OF NICOTINIC ACID N-OXIDE, THEIR PREPARATION AND THEIR USE AS INHIBITORS OF ENZYME 3-HYDROXYANTHRANILATE-3, 4-DIOXYGENASE

A derivative of nicotinic acid N-oxide is described having formula (I): that acts as inhibitor of enzyme 3-hydroxyanthranilate-3,4-dioxygenase (3HAO), and is thus able to reduce QUIN biosynthesis in vivo under excitotoxic or pathological conditions, said compound being at the same time also chemically stable towards auto-oxidation.