111253-25-9Relevant articles and documents
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.
One-Pot Expeditious Synthesis of 2-Amino-4,6-(disubstituted)nicotinonitriles Using Activated Fuller’s Earth as Catalyst
Rekunge, Deelip S.,Mali, Anil S.,Chaturbhuj, Ganesh U.
, p. 112 - 119 (2021/03/15)
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One-pot synthesis of 2-amino-3-cyanopyridines and hexahydroquinolines using eggshell-based nano-magnetic solid acid catalyst via anomeric-based oxidation
Akbarpoor, Tahere,Khazaei, Ardeshir,Seyf, Jaber Yousefi,Sarmasti, Negin,Gilan, Maryam Mahmoudiani
, p. 1539 - 1554 (2019/12/11)
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.].