Synthesis, cholinesterase inhibition and molecular modelling studies of coumarin linked thiourea derivatives

Natural products and their derivatives as multifunctional ligands against Alzheimer's disease

“…The derivative 10a has potent inhibitory activity against EeAChE (IC 50 of 0.092 μM) and moderate for EqBuChE (IC 50 of 0.234 μM), βA antiaggregation properties (67.8% inhibition at 20 μM) and also has Cu 2+ and Fe 2+ metal chelating ability due to its amide linkage (Xie, Wang, Li, Yang, & Kong, ). Further, the coumarin moiety linked with thiourea, (compound 10b ) was found the most potent AChE inhibitor with IC 50 value of 0.04 μM (Saeed et al, ). In coumarin based MTDL derivatives ( 10c and 10d ), the 6‐ and 7‐positions of coumarin are linked with alkyl spacer of different lengths with terminal diethyl amino group which leads to human AChE inhibition at nanomolar concentration (IC 50 of 11.7 nM and 12.9 nM, respectively) along with significant inhibitory activity toward βA 42 self‐aggregation around 60% and promising neuroprotective behavior, which makes this compounds a potential disease‐modifying agent (Saeed et al, ).…”

“…Further, the coumarin moiety linked with thiourea, (compound 10b ) was found the most potent AChE inhibitor with IC 50 value of 0.04 μM (Saeed et al, ). In coumarin based MTDL derivatives ( 10c and 10d ), the 6‐ and 7‐positions of coumarin are linked with alkyl spacer of different lengths with terminal diethyl amino group which leads to human AChE inhibition at nanomolar concentration (IC 50 of 11.7 nM and 12.9 nM, respectively) along with significant inhibitory activity toward βA 42 self‐aggregation around 60% and promising neuroprotective behavior, which makes this compounds a potential disease‐modifying agent (Saeed et al, ). Further, when coumarin is attached to the dithiocarbamate moiety, then compound 10e shows the best inhibitory activity toward hAChE (IC 50 of 0.027 μM) and also acts as a βA antiaggregator (40.19% at 25 μM) (Jiang et al, ).…”

The effect of chalcogen substitution on the structure and spectroscopy of 4,7-dimethyl-2H-chromen-2-one/thione analogues

“…8 Substitutions on the benzopyrone ring influence the chemical, structural 9 and biological properties of coumarins. [10][11][12] Moreover, a large degree of structural and chemical diversity is reached by introducing different heteroatoms in the 1-and/or 2-positions of the 1-benzopyran-2one group. In particular, 2-thiocoumarins are accessible from the corresponding coumarine by using an equimolar amount of p-methoxyphenylthionophosphine sulfide dimer (Lawesson's Reagent) as sulfur-transfer reagent.…”

“…/ γ C 7 -C 6 -C 8 -C 13 (58); γ S-C-O-C(42) 527 vw 521 m 532(0.1) a'' / τ C 8 -C 8 -C 10 -C 5(12); γ S-C-O-C (52); γ C 3 -C 4 -C 10 -C 12 (36) 523(1) a' / δ C 5 -C 10 -C 9 (45);δ O-C 9 -C 8(28); ν CH 3 -Py (27) 497 vw 492 w 500(1) a' / τ H-C 13 -C 7 -C 8 (83); ν CH 3 -Py (18) 458 w 464(9) a' / δ C 2 -C 3 -O (38); δ C 7 -C 8 -C 9(36) ; ν CH 3 -Ph (25); 435 w 445(7) a'' / γ O-C 10 -C 8 -C 9 (85); γ S-C-O-C (14) 384 s 386(5) a' / νC=S (60); δ C-O-C (40) 337(0.07) a' / ρ C-CH 3 -Ph (52); ρ C-CH 3 Py (48) 274(0.2) a'' / τ C 4 -C 3 -C 2 -O (62); τ ring Ph (48) 258(1) a' / δ C 2 -C 3 -C 4 (73); δ C 5 -C 6 -C 7 (27) 247(0.0004) a'' / γ CH 3 -Ph(83); γ O-C 10 -C 8 -C 9 (16) 198(1) a'' / ρ CH 3 ring Py (84); τ C 3 -C 2 -O-C 9 (16) 197 m 190(0.4) a' / δ CS (59); δ C-H ring Ph (41) 158(0.001) a'' / τ H-C 12 -C 4 -C 3 (36); τ C 3 -C 2 -O-C 9 (64) 98(2) a'' / τ C 2 -O-C 9 -C 10 (85); τ C 3 -C 2 -O-C 9 (15) 73(0.2) a' / τ S-C-O-C (12); τ ring Ph (87) 34(0.2)…”

Unraveling the Alkaline Phosphatase Inhibition, Anticancer, and Antileishmanial Potential of Coumarin–Triazolothiadiazine Hybrids: Design, Synthesis, and Molecular Docking Analysis

“…) . Taking into account these facts and our continued interest in developing useful bioactive molecules , as well as coumarin hybrids , it was considered worthwhile to undertake the synthesis of a library of bioactive coumarin–triazolothiadiazine hybrids and evaluation of their ALP inhibition, anticancer, and antileishmanial potential. In addition, molecular docking studies of these compounds have also been carried out to gain further insights into the biological properties.…”