Ultrasound assisted Cu-catalyzed decarbonylative Sonogashira coupling-cyclization strategy: Synthesis and evaluation of 3-heteroarylmethylene isoindolin-1-ones against SIRT1

Discovery of Novel N-Acylhydrazone Derivatives as Potent Inhibitors of Sirtuin-1

“…Due to the well-characterized structure, the catalytic domain of SIRT1 has been used as a target receptor for in silico screening of binding parameters of SIRT1 modulators. 44 45 46 47 48 49 50 , 58 , 61 62 63…”

“…25 Over the past years, different SIRT inhibitors have been found among various classes of compounds. 7,[26][27][28][29][30][31][32] Downregulating activity towards HDACs class III was identified in 2-anilinobenzamides (nicotinamide analogues), 33 some acetyl lysine mimics, 26 azomethines based on 2-hydroxy-1naphthaldehyde (sirtinol, JGB1714 and others analogues), 34,35 thioureas (cambinol, tenovin-6), 36,37 and thiobarbituric acid 5-ylidene derivatives, 38 bis(indolyl)maleinimides, 34 5-benzylidene-2-phenyl-1,3-dioxane-4,6-diones 39 and indole derivatives, 40,41 naphtho[2,1-b]pyrane-3ones (splitomicin and analogues), 42 thieno[3,2-d]pyrimidine-6-carboxamides, 43 2-substituted nicotinic acid ethyl esters, 44 dihydro-1,4-benzoxazine carboxamides, 45 1,5-dihydro-1H-pyrano[2,3-d]pyrimidine-2,4(3H)-diones, 46 dihydropyrano[2,3-c]pyrazole, 47 2-arylamino-3-cyanopyridines, 48 3-heteroarylmethylene isoindolin-1-ones, 49 1,8-dioxo-octahydroxanthenes, 50 highly ionized naphthylurea suramin, 51 and various substances from natural sources (amurensin G) 52 or modified natural products such as steroids. 35 Most of these compounds have been evaluated using enzymatic and cell-based assays.…”

“…Due to the well-characterized structure, the catalytic domain of SIRT1 has been used as a target receptor for in silico screening of binding parameters of SIRT1 modulators. [44][45][46][47][48][49][50]58,[61][62][63] To test whether our molecular docking approach is able to reproduce properly the correct binding mode of the cocrystallized inhibitor Ex527, we first re-docked it against the corresponding crystal structure of SIRT1 (PDB 4I5I). 58 It has been suggested that the presence of the co-factor NAD + was essential for the activity of the SIRT1 enzyme 45 so it was maintained in the binding site for the docking study.…”

Ultrasound assisted Cu-catalyzed Ullmann-Goldberg type coupling-cyclization in a single pot: Synthesis and in silico evaluation of 11H-pyrido[2,1-b]quinazolin-11-ones against SARS-CoV-2 RdRp

“…Initially, we devoted our effort to establish the optimized reaction conditions and the Ullmann-Goldberg type coupling-cyclization of ethyl 2-iodo-5-methoxybenzoate ( 1a ) with 2-aminopyridine ( 2a ) in DMSO was used as a model reaction for this purpose. Based on our past experiences [36] , CuI (10 mmol%) and Cs 2 CO 3 (1.5 mmol) was chosen as the catalyst and base, respectively in the current study. The study was initiated by carrying out the reaction at 25 and 50°C for 60 min under ultrasound.…”

Ultrasonic-assisted-synthesis of isoindolin-1-one derivatives

“…[14][15][16][17] Recent reports demonstrated that various substituted 3-methyleneisoindolin-1-ones and isoquinolin-1(2H)-ones have been generated in good yields in shorter reaction time via metal-catalyzed-cascade reaction (comprising of Sonogashira type coupling-heterocyclization reactions) under ultrasonic irradiation. [18][19][20] Due to these valuable features, the ultrasonic irradiation has been widely employed in organic synthesis and industrial process.…”