Molecular hybridization based design and synthesis of new benzo[5,6]chromeno[2,3-b]-quinolin-13(14H)-one analogs as cholinesterase inhibitors

Inhibitory potential of nitrogen, oxygen and sulfur containing heterocyclic scaffolds against acetylcholinesterase and butyrylcholinesterase

“…Tacrine's IC 50 values against AChE and BChE were 0.47 and 0.65 µM, respectively, while donepezil had IC 50 values of 0.71 and 0.31 µM respectively. All the analogs had hydrogen bond interactions with the binding site, according to docking experiments 268 ( Table 10 ).…”

Friedlӓnder's synthesis of quinolines as a pivotal step in the development of bioactive heterocyclic derivatives in the current era of medicinal chemistry

“…In recently, Baswaraju Macha and group (Macha et al, 2021) reported, ethyl 3‐amino‐1‐phenyl‐1 H ‐benzo[ f ]chromene‐2‐carboxylate ( 233 ) were refluxed with cycloketones in the presence of POCl 3 to yield 10,11,12,12a‐tetrahydro‐9 H ‐benzo[5,6] chromeno[2,3‐ b ]quinolin‐13(14 H )‐ones ( 234 ) by Friedländer synthesis (Scheme 48). All the synthesized compounds showed good in vitro inhibitory activities toward acetyl cholinesterase (AChE) and butyrylcholinesterase (BuChE) enzymes IC 50 values ranging from 0.65 ± 0.06 to 7.64 ± 0.02 µM and among them, compounds, 234i , 234o and 234r showed equal potency of standard tacrine with IC 50 values ( 234i = 0.92 ± 0.03 µM and 1.91 ± 0.02 µM), ( 234o = 0.65 ± 0.06 µM and 1.32 ± 0.06µM), and ( 234r = 0.85 ± 0.06 µM and 1.65 ± 0.06 µM) against AChE and BuChE, respectively.…”

DABCO-Promoted Cyclization of 2-Amino-4H-chromen-4-ones with 2,6-Dibenzylidenecyclohexan-1-ones for the Synthesis of Chromeno[2,3-b]tetrahydroquinoline

“…Similar to the chromene motif, the 5,6,7,8-tetrahydroquinoline framework as a privileged pharmacophore also was widely used in designed synthetic products of therapeutic applications . Recently, as significant tactics in the construction of new innovative drugs, the combination of chromene and tetrahydroquinoline frameworks has been well investigated, which these derivatives have showed specially pharmacological activities, such as antimicrobial, anticancer, and cholinesterase inhibitor . And aminochromeno­[2,3- b ]­tetrahydro­quinoline derivatives were used as a potent AChE inhibitor for the treatment of Alzheimer’s disease .…”