Crystal Structure, Synthesis and Biological Activity of Ether and Ester <i>Trans</i>-Ferulic Acid Derivatives

Abstract

The structures of methoxymethyl (E)-3-(4-hydroxy-3-methoxyphenyl)acrylate, 2; (E)-3-(3-methoxy-4-(methoxymethoxy)phenyl)acrylic acid, 3; methyl (E)-3-(4-(benzyloxy)-3-methoxyphenyl)acrylate, 4; benzyl (E)-3-(4-(benzyloxy)-3-methoxyphenyl)acrylate, 6; and (E)-3-(4-(benzyloxy)-3-methoxyphenyl)acrylic acid, 7; were established by spectroscopic and X-ray diffraction studies. Structure 2 is a new compound. Compounds with free phenolic hydroxyls v.gr. methyl (E)-3-(4-hydroxy-3-methoxyphenyl)acrylate 1, 2 and benzyl(E)-3-(4-hydroxy-3-methoxyphenyl)acrylate 5, showed scavenging freeradical and antioxidant activity while moderate scavenging free-radical was observed in compound 3. Moderate inhibition of lipid peroxidation was observed for 7. Compound 5 exerted significant inhibition of cell growth in PC-3, K562 tumor cell lines and 4 exhibited the largest cytotoxic effect upon the K562 cell line.

Non-Cytotoxic Dibenzyl and Difluoroborate Curcuminoid Fluorophores Allow Visualization of Nucleus or Cytoplasm in Bioimaging

“…Compounds 2 and 5 emerged from all derivatives after fulfilling the following criteria: (i) the improvement of the fluorescent properties preserving the conjugated system D–π–D [ 21 , 22 , 23 ] without modifying the coplanarity of curcumin’s heptanoid chain; (ii) the improvement of lipophilicity [ 24 ]; (iii) straightforward synthesis under mild reaction conditions [ 25 ]; and (iv) a substantial reduction of cytotoxicity and good reaction yield. The derivatization of phenolic functions with benzyl bromide proved to be adequate to add different properties to the curcumin scaffold.…”