74873-35-1

Upstream product

• 104-87-0 4-methyl-benzaldehyde 
• 98-86-2 acetophenone 
• 109-77-3 malononitrile 
• 2826-25-7 2-(4-methylbenzylidene)malononitrile 
• 19310-59-9 2-cyano-3-(p-tolyl)acrylamide 
• 65429-74-5 3-cyano-4-(4-methyl-phenyl)-6-phenyl-1,2-dihydro-pyridine-2-one 
• 4224-87-7 4-methyl-chalcone 
• 100-52-7 benzaldehyde 
• 57-13-6 urea 
• 613-91-2 acetophenone oxime 
• 1293990-84-7 (E)-1-phenylethan-1-one O-pivaloyl oxime 
• 19433-17-1 (E)‐1‐phenylethan‐1‐one O‐acetyl oxime 
• 156605-56-0 1-phenylethan-1-one O-pivaloyl oxime 
• 156638-73-2 2-azido-4-(4-methyl-phenyl)-6-phenyl-pyridine-3-carbonitrile 

Downstream Products

• 1370256-19-1 1-(3-cyano-6-phenyl-4-(4-methylphenyl)pyridin-2-yl)-5-oxopyrrolidine-3-carboxylic acid 

Relevant academic research and scientific papers

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.

Application of salicylic acid as an eco-friendly and efficient catalyst for the synthesis of 2,4,6-triaryl pyridine, 2-amino-3-cyanopyridine, and polyhydroquinoline derivatives

In this study, three eco-friendly, efficient, and convenient protocols have been reported for one-pot synthesis of 2,4,6-triaryl pyridine, 2-amino-3-cyanopyridine, and polyhydroquinoline derivatives using salicylic acid as a catalyst under solvent-free condition. The reported protocols offer several significant advantages such as the application of a nontoxic, neutral, and cheap catalyst, environmentally friendly conditions, the easy isolation of products by filtering, short reaction times, simple methodology, and good yields.

Green synthesis of 2-amino-3-cyanopyridines via a cooperative vinylogous anomeric-based oxidation and their antiproliferative effects on liver, breast, and prostate cancer studies

2-Amino-3-cyanopyridine derivatives were synthesized in an ultrasonic bath and one pot four-component reactions with high yields, in a short time, without solvent and catalyst, and anticancer activity studies on MCF7, DU145, and HepG2 cell lines were inve

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.

Unveiling the urease like intrinsic catalytic activities of two dinuclear nickel complexes towards thein situsyntheses of aminocyanopyridines

Designing metal complexes as functional models for metalloenzymes remains one of the main targets in synthetic bioinorganic chemistry. Furthermore, the utilization of the product(s) derived from the catalytic reaction for subsequent organic transformation

Facile microwave-assisted preparation of an ester-based cationic gemini surfactant for the improved micellar synthesis of aminocyanopyridines

In this work, a diester cationic gemini surfactant (DCGS) was prepared from the reaction of N,N-dimethyldodecylamine with the microwave (MW)-assisted synthesized spacer ethane-1,2-diyl bis(2-chloroacetate) (EDBC) by the three-component reaction of ethylene glycol with chloroacetic acid (2 equiv.) under MW-irradiation. The structure of the spacer EDBC and surfactant DCGS were evaluated by 1H NMR, FT-IR, melting point, surface tension (γ), pendant drop, and critical micelle concentration (CMC) analysis and also cleavability test for DCGS. The γ and CMC for DCGS were 36.8 (～50% γ H2O) and 1.62 × 10?5 mol L?1 and lower than simple GSs. The catalytic performance of DCGS was evaluated in the synthesis of aminocyanopyridines by the four-component reaction of acetophenone, malononitrile, (NH4)2CO3, and aldehydes in water. Thermal stability, easy separation and highest ever reported turnover number (TON) and turnover frequency (TOF) for synthesis of products are advantages of DCCGS.

Poly N,N-dimethylaniline-formaldehyde supported on silica-coated magnetic nanoparticles: a novel and retrievable catalyst for green synthesis of 2-amino-3-cyanopyridines

Preparation and application of novel and reusable magnetic nanoparticles with poly N,N-dimethylaniline-formaldehyde support as a heterogeneous basic catalyst have been described. The reported catalyst was characterized by Fourier transform infrared spectr

One-pot synthesis of 2-amino-3-cyanopyridines and hexahydroquinolines using eggshell-based nano-magnetic solid acid catalyst via anomeric-based oxidation

Abstract: In the present research, the eggshell as a hazardous waste by European Union regulations was converted to a valuable catalyst, namely nano-Fe3O4@(HSO4)2. The as-prepared catalyst, first, was characterized using different techniques, including Fourier-transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), energy-dispersive X-ray spectroscopy (EDX), field emission scanning electron microscopy (FESEM), and transmission electron microscopy (TEM). Back-titration method confirmed the loading of a high surface density of acidic group, namely 8.8?mmol HSO4 per gram of the catalyst. The catalytic property of the as-prepared catalyst was examined in the synthesis of 2-amino-3-cyanopyridines via anomeric-based oxidation (ABO), and hexahydroquinolines derivatives. High yield, short reaction time, solvent-free condition, waste to wealth, and optimization with the design of experiment are the major advantages of the present work. Taken together, these results suggest the conversion of waste to wealth products around the world and usage in organic transformation. Graphic abstract: [Figure not available: see fulltext.].

Sulfonic acid-functionalized graphitic carbon nitride composite: a novel and reusable catalyst for the one-pot synthesis of polysubstituted pyridine in water under sonication

Graphitic carbon nitride as an interesting sustainable soft nanomaterial has drawn broad interdisciplinary attention because of unique electronic structure and chemical stability. An ultrasound-assisted preparation of a series of polysubstituted pyridines

Apoptosis: A target for anticancer therapy with novel cyanopyridines

One of the many methods of treating cancer is to terminate the uncontrolled growth of cancer cells. So, aiming the apoptotic pathway is an exciting approach to finding new anticancer agents. A novel series of cyanopyridines was designed and synthesized for antiproliferative evaluation. 2-Amino-6-(4-(benzyloxy)phenyl)-4-(4-(dimethylamino)phenyl) nicotinonitrile 10f was the most potent inhibitor against the growth of PC-3, and HepG-2 cancer cell lines with IC50 values of 2.04 uM (selectivity index, SI = 78.63, 43, respectively). Also, 10f was safe against the growth of normal human diploid lung fibroblasts cell line (WI-38) with an IC50 value of 160.04 uM. Its analogs, 10b, 10d, 10g, and 11b, were also active against the growth of PC-3, and HepG-2 while against MCF-7 cell line, they displayed good cytotoxic activity compared to the reference standard 5-FU. Remarkably, mechanistic studies indicated that compounds 10b, 10d, 10f, 10g, and 11b stimulated the level of active caspase 3 and boosted the BAX/BCL2 ratio 20–95 folds in comparison to the control. Our results have also indicated that 10b, 10d, 10f, 10g, and 11b exhibited a very potent inhibitory activity against PIM-1 kinase enzyme, where the IC50 values unraveled very potent molecules in the micromolar range (0.47–1.27 μM). Further investigations have shown that 10f, the most potent PIM-1 kinase inhibitor, induced a cell cycle arrest at the G2/M phase. Moreover, in silico evaluation of ADME properties indicated that all the cyanopyridine compounds are orally bioavailable with no permeation to the blood brain barrier.