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Crystal Structure, Synthesis and Biological Activity of Ether and Ester Trans-Ferulic Acid Derivatives

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DOI: 10.4236/ijoc.2018.84028    341 Downloads   766 Views

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.

Cite this paper

Obregón-Mendoza, M. , Estévez-Carmona, M. , Alvarez-Ricardo, Y. , Meza-Morales, W. , Escobedo-Martínez, C. , Soriano-García, M. and Enríquez, R. (2018) Crystal Structure, Synthesis and Biological Activity of Ether and Ester Trans-Ferulic Acid Derivatives. International Journal of Organic Chemistry, 8, 359-377. doi: 10.4236/ijoc.2018.84028.

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