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

doi:10.1016/j.ejmech.2009.03.011

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

Department of Molecular Medicine

Research output: Contribution to journal › Article › peer-review

53 Scopus citations

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 language	English
Pages (from-to)	3166-3174
Number of pages	9
Journal	European Journal of Medicinal Chemistry
Volume	44
Issue number	8
DOIs	https://doi.org/10.1016/j.ejmech.2009.03.011
State	Published - Aug 2009

Keywords

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

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10.1016/j.ejmech.2009.03.011

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@article{f6ec9b3535c84f8096a21d1a36d6f2ab,

title = "Synthesis of novel trans-stilbene derivatives and evaluation of their potent antioxidant and neuroprotective effects",

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.",

keywords = "Free radical-scavenging effects, LPS-induced NO generation, Neuroprotective activity, Wittig-Horner reaction, trans-Stilbene derivatives",

author = "Jung, {Jae Chul} and Eunyoung Lim and Yongnam Lee and Kang, {Jun Mo} and Heejeong Kim and Soyong Jang and Seikwan Oh and Mankil Jung",

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. ",

year = "2009",

month = aug,

doi = "10.1016/j.ejmech.2009.03.011",

language = "English",

volume = "44",

pages = "3166--3174",

journal = "European Journal of Medicinal Chemistry",

issn = "0223-5234",

publisher = "Elsevier Masson s.r.l.",

number = "8",

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TY - JOUR

T1 - Synthesis of novel trans-stilbene derivatives and evaluation of their potent antioxidant and neuroprotective effects

AU - Jung, Jae Chul

AU - Lim, Eunyoung

AU - Lee, Yongnam

AU - Kang, Jun Mo

AU - Kim, Heejeong

AU - Jang, Soyong

AU - Oh, Seikwan

AU - Jung, Mankil

N1 - 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.

PY - 2009/8

Y1 - 2009/8

N2 - 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.

AB - 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.

KW - Free radical-scavenging effects

KW - LPS-induced NO generation

KW - Neuroprotective activity

KW - Wittig-Horner reaction

KW - trans-Stilbene derivatives

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M3 - Article

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AN - SCOPUS:67349183313

SN - 0223-5234

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SP - 3166

EP - 3174

JO - European Journal of Medicinal Chemistry

JF - European Journal of Medicinal Chemistry

IS - 8

ER -

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

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Keywords

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