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

¹ Instituto de Química, Universidad Nacional Autónoma de México, Ciudad de México, México
² Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, México City, México
³ Instituto de Química, Universidad Nacional Autónoma de México, Ciudad de México, México
⁴ Instituto de Química, Universidad Nacional Autónoma de México, Ciudad de México, México
⁵ Departamento de Farmacia, División de Ciencias Naturales y Exactas, Universidad de Guanajuato, Guanajuato, México
⁶ Instituto de Química, Universidad Nacional Autónoma de México, Ciudad de México, México
⁷ Instituto de Química, Universidad Nacional Autónoma de México, Ciudad de México, México

International Journal of Organic Chemistry·Volume 08 (2018)·Pages 359–377·Published 24 October 2018·DOI10.4236/ijoc.2018.84028

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.

Keywords&lti&gtTrans&lt/i&gt-Ferulic AcidCrystal StructuresAntioxidant ActivityAntitumorScavenging Free-Radicals

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

Abstract

References (29)