74873-41-9Relevant academic research and scientific papers
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.
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.].
Dual C(sp3)-H Functionalization of Cyclic Ethers via Singlet Oxygen-Mediated Ring Opening and Ring Closing
Yuan, Xu,Yu, Xianglin,He, Kun,Zhang, Ruihan,Xiao, Weilie,Lin, Jun,Zhan, Zhajun,Cheng, Xiaohong,Shao, Zhihui,Jin, Yi
, p. 8267 - 8272 (2021/10/25)
A metal-free dual C(sp3)-H bond functionalization of saturated cyclic ethers via photooxidative singlet oxygen-mediated ring opening and ring closing has been developed, providing a method for generating hydrobenzofurans/pyrans/dioxins. Mechanistic studies have confirmed that ring-opening intermediates were effectively generated by singlet oxygen-mediated C(sp3)-H activation and efficiently reacted with aldehydes and activated methylene compounds to form a wide array of products with high diastereoselectivities (up to >95:5 dr). This study is a rare example of α,β-dual C(sp3)-H bond functionalization of ethers.
Sulfonic acid-functionalized graphitic carbon nitride composite: a novel and reusable catalyst for the one-pot synthesis of polysubstituted pyridine in water under sonication
Edrisi, Mahtab,Azizi, Najmedin
, p. 901 - 910 (2019/12/27)
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
Synthesis of cobalt tetra-2,3-pyridiniumporphyrazinato with sulfonic acid tags as an efficient catalyst and its application for the synthesis of bicyclic: Ortho -aminocarbonitriles, cyclohexa-1,3-dienamines and 2-amino-3-cyanopyridines
Baghery, Saeed,Dashteh, Mohammad,Khazaei, Ardeshir,Makhdoomi, Sajjad,Safaiee, Maliheh,Yarie, Meysam,Zolfigol, Mohammad Ali
, p. 27824 - 27834 (2020/08/17)
Cobalt tetra-2,3-pyridiniumporphyrazinato with sulfonic acid tag [Co(TPPASO3H)]Cl was produced and catalyzed the synthesis of ortho-aminocarbonitriles, cyclohexa-1,3-dienamines and 2-amino-3-cyanopyridines. The synthesis of 2-amino-3-cyanopyridines by usi
Poly N,N-dimethylaniline-formaldehyde supported on silica-coated magnetic nanoparticles: a novel and retrievable catalyst for green synthesis of 2-amino-3-cyanopyridines
Asadbegi, Sajad,Bodaghifard, Mohammad Ali,Mobinikhaledi, Akbar
, p. 1629 - 1643 (2017/11/28)
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
Synthesis and anticholinesterase activity of novel non-hepatotoxic naphthyridine-11-amine derivatives
Zengin Kurt, Belma
, p. 625 - 638 (2018/12/11)
Abstract: In the present study, 14 novel naphthyridine-11-amine derivatives were synthesized and their inhibitory effects on acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) were evaluated. 12-(4-Fluorophenyl)-1,2,3,4,7,8,9,10-octahydrodibenz
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
Afradi, Mojgan,Pour, Sjjad Abbasi,Dolat, Maryam,Yazdani-Elah-Abadi, Afshin
, (2017/10/24)
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.
Graphene oxide: A reusable and metal-free carbocatalyst for the one-pot synthesis of 2-amino-3-cyanopyridines in water
Khalili, Dariush
, p. 1721 - 1723 (2016/04/04)
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.
A multicomponent synthesis of 2-amino-3-cyanopyridine derivatives catalyzed by heterogeneous and recyclable copper nanoparticles on charcoal
Khalifeh, Reza,Ghamari, Mahdiyeh
, p. 759 - 768 (2016/04/20)
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.
