Synthesis of novel trans-stilbene derivatives and evaluation of their potent antioxidant and neuroprotective effects

Jae Chul Jung, Eunyoung Lim, Yongnam Lee, Jun Mo Kang, Heejeong Kim, Soyong Jang, Seikwan Oh, Mankil Jung

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Abstract

A convenient synthesis and the biological properties of new amides, esters and other derivatives of trans-stilbene are described. The key synthetic strategies involve the Wittig-Horner reaction of a phosphonium salt 9 and an aldehyde 10 to generate (E)- or (Z)-olefins and a coupling reaction of an acid 12 and various amines 13a-n to give trans-stilbene derivatives 15a-n in high yields. A amide derivative 15g showed three times more in vitro free radical-scavenging activity than resveratrol, while another 15d exhibited strong inhibitory activity against lipopolysaccharide (LPS)a-induced NO generation. Allylamide analogue 15a showed the most potent neuroprotective activity in glutamate-induced primary cortical neuron cells.

Original languageEnglish
Pages (from-to)3166-3174
Number of pages9
JournalEuropean Journal of Medicinal Chemistry
Volume44
Issue number8
DOIs
StatePublished - Aug 2009

Bibliographical note

Funding Information:
This work was supported by a KOSEF Brain Neurobiology Grant (2007), Ewha Global Challenge (BK21) grant, grant (20070301-034-026-007-04-00) from the BioGreen 21 Program, Rural Development Administration, and Korean Research Foundation Grant funded by the Korean Government (MOEHRD) (KRF-2006-312-C00267), the Republic of Korea. E.L. and Y.L. received fellowships from the BK 21 program of the Ministry of Education and Human Resources Development, the Republic of Korea and the Seoul Science Fellowship Program.

Keywords

  • Free radical-scavenging effects
  • LPS-induced NO generation
  • Neuroprotective activity
  • Wittig-Horner reaction
  • trans-Stilbene derivatives

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