TITLE:
Crystal Structure, Synthesis and Biological Activity of Ether and Ester Trans-Ferulic Acid Derivatives
AUTHORS:
Marco A. Obregón-Mendoza, M. Mirian Estévez-Carmona, Yair Alvarez-Ricardo, William Meza-Morales, Carolina Escobedo-Martínez, Manuel Soriano-García, Raúl G. Enríquez
KEYWORDS:
Trans-Ferulic Acid, Crystal Structures, Antioxidant Activity, Antitumor, Scavenging Free-Radicals
JOURNAL NAME:
International Journal of Organic Chemistry,
Vol.8 No.4,
December
14,
2018
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 com-pound. Compounds with free phenolic hydroxyls v.gr. methyl (E)-3-(4-hydroxy-3-methoxyphenyl)acrylate 1, 2 and ben-zyl(E)-3-(4-hydroxy-3-methoxyphenyl)acrylate 5, showed scavenging free- radical 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.