No abstract

These authors contributed equally to this work.Tryptamine-triazole hybrid compounds (11-18) were synthesized via click reaction between tryptamine azide and propargylated natural compounds. Their cholinesterase inhibitory activity was evaluated. Among the eight compounds, compound 11 showed the most potent inhibitory activity [IC 50 = 0.42 AE 0.29 μM for equine butyrylcholinesterase (BuChE) and 1.96 AE 0.15 μM for human BuChE]. From the molecular modeling study, compound 11 was bound to the catalytic anionic site, anionic subsite, peripheral anionic subsite, acyl-binding pocket, and oxyanion hole of human or horse BuChE by forming a hairpin or U-shaped structure. The Lineweaver-Burk plot of compound 11 against BuChE suggests a mixed type of inhibition which corresponds well with the molecular modeling study.

2‐Amino‐substituted‐1,4‐naphthoquinone derivatives (10–17) were synthesized from coupling reaction between 1,4‐dihydroxynaphthalene and amines in the presence of catalyst CeCl3.7H2O. Their anticancer activity was evaluated by using three ovarian cancer cells (A2780, SKOV3, and OVCAR3). Among the eight compounds, compound 13 containing metal chelating moiety had a relatively potent cytotoxic activity (IC50 < 10 μM) on all three ovarian cancer cells.

Honokiol-triazole derivatives (4-17) were synthesized via click reactions between 2-or 4 0 -propargylated honokiol and azide compounds. Their anticancer activities were evaluated by using two ovarian cancer cells (A2780 and OVCAR3). Among the 14 compounds, compound 5 coupled with 4 0 -propargylated honokiol and benzyl azide exhibited relatively potent cytotoxic activity (IC 50 = 5.5 AE 0.5 μM for A2780 and IC 50 = 3.97 AE 0.6 μM for OVCAR3) but was less toxic to normal cells (IC 50 = 18.90 AE 0.9 μM for IOSE80PC). The cytotoxic effect of compound 5 is associated with caspase-dependent apoptotic cell death via induction of intracellular reactive oxygen species. 1 H NMR (400 MHz, CDCl 3 ): δ 3.34 (d, J = 6.8 Hz, 2H), 3.39 (d, J = 6.8 Hz, 2H), 4.97-5.18 (m, 4H), 5.13 (s, 1H), 5.25 (s, 2H), 5.56 (s, 2H), 5.88-6.00 (m, 2H), 6.89 (d, J = 8.4 Hz, 1H), 7.02 (d, J = 8.4 Hz, 2H), 7.06 (d,