Synthesis and antiproliferative activity of cyclic arylidene ketones: a direct comparison of monobenzylidene and dibenzylidene derivatives

Synthesis of Dicarbonyl Curcumin Analogues Containing the Tropane Scaffold

“…Introducing nitrogen into the structure of curcumin analogues introduces a secondary binding site (a hydrogen‐bond acceptor) . Nitrogen modified compounds showed better free radical activity, activity against cancer cell lines and improves solubility behavior . Previously the effect of nitrogen introduced in a form of 4‐piperidone structure to curcumin analogues was studied , .…”

“…Moreover, it was demonstrated that addition of thiols (a known mechanism of protein binding) to α,β‐unsaturated‐β′‐amino ketones (enones with additional β amino nitrogen) was significantly faster than addition to unmodified enones . Nitrogen containing derivatives including N‐methyl derivatives showed improved antiproliferative activities compared with homocyclic congeners . Moreover, fusing the diarylheptanoid characteristic of curcumin with a structure representative of a group of natural products such as tropanes, many of which possess biological activities, could give interesting results.…”

A novel cluster of C5-curcuminoids: design, synthesis, in vitro antiproliferative activity and DNA binding of bis(arylidene)-4-cyclanone derivatives based on 4-hydroxycyclohexanone scaffold

“…Our purpose is to give further insight into the influence of structural modifications at position 4 of the cyclic ketone scaffold on the biological effect. We proved among other things [28] that this position, being an auxiliary binding ability (secondary pharmacophore) to the in vivo biological site of action, has great influence on the cytotoxicity of these compounds. In other words, the binding strength of the C 5 -curcuminoids to the biological site of action is weak when merely the pentadienone moiety reacts.…”

“…1). In one of our previous publications, we compared the antiproliferative activity of 25 arylidene cyclanones where the ketone scaffold was cyclopentanone, cyclohexanone, 1-indanone, 1-tetralone or 4-piperidone (2, X = CH 2 , NH or N-alkil) [28]. Their cytotoxicity against four human adherent cancer cell lines was evaluated.…”

(E)-2-Benzylidenecycloalkanones XII.* Kinetic Measurement of Bovine and Human Serum Albumine Interaction with Selected Chalcones and Their Cyclic Chalcone Analogues by UV Spectrophotometry

“…Chalcones (1) are intermediary compounds of the biosynthetic pathway of a very large and widespread group of plant constituents known collectively as flavonoids [2]. Among the naturally occurring chalcones and their synthetic analogues, several compounds displayed antineoplastic activity [2] [3].…”