4604-06-2Relevant academic research and scientific papers
Cu(OAc)2 as a green promoter for one-pot synthesis of 2-amino-4,6-diarylpyridine-3-carbonitrile as antibacterial agents
Fatemeh Mirjalili, Bi Bi,Gholami, Ahmad,Kalantari, Nematallah,Khabnadideh, Soghra,Nezamalhosseini, Seyed Mohammad,Zamani, Leila
, p. 149 - 156 (2020)
The extensive use of antimicrobial drugs and their resistance against bacterial infections have led to discover new antimicrobial compounds. In this study, we wish to report, one-pot synthesis of 2-amino-3-cyanopyridine derivatives (1a-14a). These compoun
A convenient method for preparation of 2-amino-4,6-diphenylnicotinonitrile using HBF4 as an efficient catalyst via an anomeric based oxidation: A joint experimental and theoretical study
Zolfigol, Mohammad Ali,Kiafar, Mahya,Yarie, Meysam,Taherpour, Avat(Arman),Fellowes, Thomas,Nicole Hancok, Amber,Yari, Ako
, p. 674 - 680 (2017)
Experimental and computational studies in the synthesis of 2-amino-4,6-diphenylnicotinonitrile using HBF4 as an oxidizing promoter catalyst under mild and solvent free conditions were carried out. The suggested anomeric based oxidation (ABO) me
Chalcone-inspired rA1/A2A adenosine receptor ligands: Ring closure as an alternative to a reactive substructure
Aucamp, Janine,Janse van Rensburg, Helena D.,Legoabe, Lesetja J.,Matthee, Chrisna,Terre’Blanche, Gisella
, (2021/12/30)
Over the past few years, great progress has been made in the development of high-affinity adenosine A1 and/or A2A receptor antagonists—promising agents for the potential treatment of Parkinson's disease. Unfortunately, many of these compounds raise structure-related concerns. The present study investigated the effect of ring closures on the rA1/A2A affinity of compounds containing a highly reactive α,β-unsaturated carbonyl system, hence providing insight into the potential of heterocycles to address these concerns. A total of 12 heterocyclic compounds were synthesised and evaluated in silico and in vitro. The test compounds performed well upon qualitative assessment of drug-likeness and were generally found to be free from potentially problematic fragments. Most also showed low/weak cytotoxicity. Results from radioligand binding experiments confirm that heterocycles (particularly 2-substituted 3-cyanopyridines) can replace the promiscuous α,β-unsaturated ketone functional group without compromising A1/A2A affinity. Structure–activity relationships highlighted the importance of hydrogen bonds in binding to the receptors of interest. Compounds 3c (rA1Ki?=?16?nM; rA2AKi?=?65?nM) and 8a (rA1Ki?=?102?nM; rA2AKi?=?37?nM), which both act as A1 antagonists, showed significant dual A1/A2A affinity and may, therefore, inspire further investigation into heterocycles as potentially safe and potent adenosine receptor antagonists.
Amberlyst-15 catalysed sonochemical synthesis of 2-amino-4,6-disubstituted nicotinonitrile derivatives and their biological evaluation
Challa, Chandra Sekhar,Katari, Naresh Kumar,Nallanchakravarthula, Varadacharyulu,Nayakanti, Devanna,Kapavarapu, Ravikumar,Pal, Manojit
, (2021/06/07)
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.
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
Roozifar, Majid,Hazeri, Nourallah,Faroughi Niya, Homayoun
, p. 1117 - 1129 (2021/02/26)
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.
β-Cyclodextrin: A supramolecular catalyst for metal-free approach towards the synthesis of 2-amino-4,6-diphenylnicotinonitriles and 2,3-dihydroquinazolin-4(1 H)-one
Mitra, Bijeta,Chandra Pariyar, Gyan,Ghosh, Pranab
, p. 1271 - 1281 (2021/01/20)
β-Cyclodextrin, a green and widespread supramolecular catalyst, has been explored as a highly proficient promoter for the metal-free one-pot multi-component synthesis of a vast range of highly functionalized bioactive heterocyclic moiety, 2-amino-4,6-diphenylnicotinonitriles and 2,3-dihydroquinazolin-4(1H)-one, from easily available precursor aldehydes. The main endeavor of these protocols is to explore this organic supramolecule in one-pot multi-component synthesis. Absence of metal catalyst or toxic acid and harsh reaction conditions, excellent functional group tolerance, inexpensive, greener and environmentally safe protocol are the key advantages of this work.
Synthesis of a novel acidic ionic liquid catalyst and its application for preparation of pyridines via a cooperative vinylogous anomeric-based oxidation
Rahmati, Mohammad,Habibi, Davood
, p. 1643 - 1661 (2021/01/20)
Abstract: In the current study, a novel acidic ionic liquid catalyst based on 8-hydroxyquinoline, namely 8,8′,8″-([1,3,5-triazine-2,4,6-triyl]tris[oxy])tris(1-sulfoquinolin-1-ium)chloride (TTS), was designed and synthesized. The structure of the prepared acidic ionic liquid (AIL) was fully investigated by using Fourier transform infrared (FT-IR) spectroscopy, energy dispersive X-ray (EDX) analysis, thermogravimetric analysis/differential thermal analysis (TGA/DTA), 1HNMR, 13CNMR and mass spectroscopy. Then, the catalytic performance of described AIL was successfully inspected toward the four-component synthesis of pyridine derivatives via a cooperative vinylogous anomeric-based oxidation. Graphic abstract: Novel AIL (TTS) showed a very high efficiency in the synthesis of pyridines. [Figure not available: see fulltext.].
Unveiling the urease like intrinsic catalytic activities of two dinuclear nickel complexes towards thein situsyntheses of aminocyanopyridines
Kundu, Bidyut Kumar,Pragti,Biswas, Soumen,Mondal, Abhijit,Mazumdar, Shyamalava,Mobin, Shaikh M.,Mukhopadhyay, Suman
, p. 4848 - 4858 (2021/04/22)
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
Synthesis, characterization, and application of CoFe2O4@TRIS@sulfated boric acid nanocatalyst for the synthesis of 2-amino-3-cyanopyridine derivatives
Faroughi Niya, Homayoun,Hazeri, Nourallah,Maghsoodlou, Malek Taher,Fatahpour, Maryam
, p. 1315 - 1330 (2021/02/11)
Abstract: The aim of this research is the synthesis of a novel acidic nanocatalyst using the layer-by-layer assembly technique. The CoFe2O4@TRIS@sulfated boric acid nanoparticles were easily synthesized and studied as a highly beneficial, recyclable, and magnetite nanocatalyst for the synthesis of 2-amino-3-cyanopyridine derivatives. The chemical structure of CoFe2O4@TRIS @sulfated boric acid nanocatalyst was completely confirmed with different techniques like FESEM, Map, EDS, XRD, TGA/DTG, VSM, and FT-IR analyses. Briefly, the newly synthesized nanocatalyst offers some advantages such as simplicity of work-up, highly stable, environmental friendliness, reusability, excellent yields, and short reaction time. Graphic abstract: [Figure not available: see fulltext.].
Apoptosis: A target for anticancer therapy with novel cyanopyridines
Ismail, Magda M.F.,Farrag, Amel M.,Harras, Marwa F.,Ibrahim, Mona H.,Mehany, Ahmed B.M.
, (2019/12/25)
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.
