18631-33-9

Upstream product

• 100-52-7 benzaldehyde 
• 67-64-1 acetone 
• 109-77-3 malononitrile 
• 98-86-2 acetophenone 
• 15270-98-1 C₁₃H₁₀N₂ 
• 83655-36-1 1,4-methyl-6-phenyl-2(1H)-pyrimidinethione 
• 74360-15-9 1,6-diphenyl-4-methyl-2-(1H)pyrimidinethione 
• 55244-11-6 ethyl cyanoacetimidate hydrochloride 
• 1896-62-4 (E)-benzalacetone 
• 122-57-6 1-Phenylbut-1-en-3-one 
• 2700-22-3 Benzylidenemalononitrile 

Downstream Products

• 1391062-95-5 2-amino-4-phenyl-6-methylnicotinonitrile N-oxide 
• 1391062-90-0 2-amino-4-phenyl-6-methylnicotinic acid N-oxide 

Relevant academic research and scientific papers

2-Aminopyridine derivative as fluorescence 'On-Off' molecular switch for selective detection of Fe3+/Hg2+

2-Amino-6-methyl-4-phenyl-nicotinonitrile 1, a 2-aminopyridine-based fluorescent compound, was found to be a fluorescent chemosensor for the detection of Fe3+ and Hg2+ ions over a number of other metal ions. Compound 1 was synthesized in one step using a multicomponent reaction, and characterized using common spectroscopic tools. During Fe 3+/Hg2+ sensing the compound 1 followed a 'switch-off' mechanism. Further, compound 1 could sense Fe3+ over Hg2+ by its distinct absorption and fluorescence quenching behaviors. 1:1 complex formation of 1 with Fe3+ and Hg2+ was clearly understood from Job's plot. The present work brings additional evidence on the importance of multicomponent reactions which could lead to the development of fluorescence chemosensor in one step for the selective detection of biologically important metal ions.

Amberlyst-15 catalysed sonochemical synthesis of 2-amino-4,6-disubstituted nicotinonitrile derivatives and their biological evaluation

The 2-amino nicotinonitrile framework has been explored first time for the identification of potential inhibitors of SIRT1. Thus a series of targeted 2-amino-4,6-disubstituted nicotinonitrile derivatives were synthesized by employing an ultrasound assisted MCR of ketones, aldehydes, malononitrile and ammonium acetate. The MCR was carried out in the presence of Amberlyst-15 in MeCN under mild conditions to give the desired product in good yields. The reaction was less efficient in the absence of air whereas combination of Amberlyst-15, ultrasound, air and MeCN was essential for the success of this MCR. Several of the synthesized compounds showed good activities when tested for their SIRT1 inhibitory potential in vitro among which 5c, 5e and 5n were identified as the most potent (IC50 ~ 3 μM) and were better than the known inhibitor nicotinamide (IC50 ~109 μM). In the in silico docking studies these three compounds showed better binding energy (> 100 kcal/mol) and higher number of interactions than nicotinamide (binding energy -88.38 kcal/mol). While both amino (–NH2) and cyano (–CN) groups of nicotinonitrile derivatives formed H-bonds with the ASN346 and HIS363 residue respectively the nicotinamide showed similar interactions with ASP348 and ILE347 through its amide (–CONH2) moiety. Compound 5c, 5e and 5n has been identified as initial hits for further study.

Synthesis of a novel and reusable biological urea based acidic nanomagnetic catalyst: Application for the synthesis of 2-amino-3-cyano pyridines via cooperative vinylogous anomeric based oxidation

In the current study, a novel and reusable biological urea based nano magnetic catalyst namely Fe3O4@SiO2@(CH2)3-urea-benzimidazole sulfonic acid was designed and synthesized. The structure of the titled catalyst was fully characterized using several skills including Fourier transform infrared (FT-IR) spectroscopy, energy dispersive X-ray (EDX) analysis, X-ray diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), thermo gravimetric analysis/differential thermal analysis (TG/DTG) and vibrating sample magnetometer (VSM). Then, the catalytic performance of Fe3O4@SiO2@(CH2)3-urea-benzimidazole sulfonic acid was successfully inspected towards the multicomponent synthesis of 2-amino-3-cyano pyridine derivatives through a vinylogous anomeric based oxidation pathway.

Synthesis of a novel and reusable biological urea based acidic nanomagnetic catalyst: Application for the synthesis of 2-amino-3-cyano pyridines via cooperative vinylogous anomeric based oxidation

In the current study, a novel and reusable biological urea based nano magnetic catalyst namely Fe3O4@SiO2@(CH2)3-urea-benzimidazole sulfonic acid was designed and synthesized. The structure of the titled catalyst was fully characterized using several skills including Fourier transform infrared (FT-IR) spectroscopy, energy dispersive X-ray (EDX) analysis, X-ray diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), thermo gravimetric analysis/differential thermal analysis (TG/DTG) and vibrating sample magnetometer (VSM). Then, the catalytic performance of Fe3O4@SiO2@(CH2)3-urea-benzimidazole sulfonic acid was successfully inspected towards the multicomponent synthesis of 2-amino-3-cyano pyridine derivatives through a vinylogous anomeric based oxidation pathway.

Nanomagnetically modified vitamin B3 (Fe3O4@Niacin): An efficient and reusable green biocatalyst for microwave-assisted rapid synthesis of 2-amino-3-cyanopyridines in aqueous medium

Superparamagnetic nanoparticles of modified vitamin B3 (Fe3O4@Niacin) represent a new, efficient and green biocatalyst for the one-pot synthesis of 2-amino-3-cyanopyridine derivatives via four-component condensation reaction between aldehydes, ketones, malononitrile, and ammonium acetate under microwave irradiation in water. This new magnetic organocatalyst was easily isolated from the reaction mixture by magnetic decantation using an external magnet and reused at least six times without significant degradation in the activity. The catalyst was fully characterized by FT-IR, XRD, SEM, VSM, UV–Vis, DLS and EDS. Excellent yield, very short reaction time (7–10?min), operational simplicity, easy work-up procedure, avoidance of hazardous or toxic catalysts and organic solvents are the main advantages of this green methodology which makes it more economic than the other conventional methods.

A multicomponent synthesis of 2-amino-3-cyanopyridine derivatives catalyzed by heterogeneous and recyclable copper nanoparticles on charcoal

An efficient and convenient method was developed for synthesis of 2-amino-3-cyanopyridine derivatives via the four-component coupling reaction between ketone, aldehyde, malononitrile, and ammonium acetate in the presence of 2 molpercent copper nanoparticles on charcoal (Cu/C) catalyst. A variety of ketones and aldehydes was used to afford the corresponding products in good to excellent yields. The method is applicable to large-scale operation without any problem. The catalyst could be quantitatively recovered from the reaction mixture by simple filtration and reused at least eight times with almost consistent activity.

Highly efficient four-component synthesis of 2-amino-3-cyanopyridines using doped nano-sized copper(I) oxide (Cu2O) on melamine-formaldehyde resin

A convenient and facile four-component synthesis is described of 2-amino-3-cyanopyridine derivatives from readily available starting materials catalysed by doped nano-sized Cu2O on melamine-formaldehyde resin (nano-Cu2O-MFR). In this method, treatment of different aldehydes, ketones, malononitrile, and ammonium acetate in refluxing H2O/EtOH (1:1) in the presence of doped nano-Cu2O-MFR as a highly efficient heterogeneous catalyst affords the corresponding 2-amino-3-cyanopyridines in good to excellent yields. The nano-Cu2O-MFR is a cheap and stable nano-catalyst that could be easily recovered and reused for many consecutive reaction runs without considerable decrease in its activity.

Graphene oxide: A reusable and metal-free carbocatalyst for the one-pot synthesis of 2-amino-3-cyanopyridines in water

A one-pot synthesis of 2-amino-3-cyanopyridine derivatives has been demonstrated through the multicomponent reaction of aldehydes, ketones, malononitrile, and ammonium acetate using graphene oxide as a heterogeneous catalyst in water as a green medium. The graphene oxide catalyst is very mild, effective, and most of its activity is preserved after being reused for five times.

[5C + 1N] Annulation of 2,4-pentadienenitriles with hydroxylamine: A synthetic route to multi-substituted 2-aminopyridines

A facile and efficient synthetic route to multi-substituted 2-aminopyridines has been developed via a formal [5C + 1N] annulation of readily available 2,4-pentadienenitriles with hydroxylamine (NH2OH) under very mild conditions, which involves

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.