Design, synthesis, and biological evaluation of 3,4,5-trimethoxyphenyl acrylamides as antinarcotic agents

Jae Chul Jung; Dongguk Min; Heejeong Kim; Soyong Jang; Yongnam Lee; Wookyu Park; Ikhlas A. Khan; Hyung In Moon; Mankil Jung; Seikwan Oh

doi:10.3109/14756360902932784

Design, synthesis, and biological evaluation of 3,4,5-trimethoxyphenyl acrylamides as antinarcotic agents

Jae Chul Jung, Dongguk Min, Heejeong Kim, Soyong Jang, Yongnam Lee, Wookyu Park, Ikhlas A. Khan, Hyung In Moon, Mankil Jung, Seikwan Oh

Department of Molecular Medicine

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

8 Scopus citations

Abstract

The synthesis and biological evaluation of 3,4,5-trimethoxyphenyl acrylamides 1af as novel antinarcotic agents are described. The molecules were prepared by the Wittig reaction, followed by a coupling reaction between 3,4,5-trimethoxycinnamic acid (9) and aliphatic amines, which resulted in good yields. When tested for biological activity, compounds 1df exhibited strong inhibitory effects on the morphine withdrawal syndrome in mice due to their high binding affinities with serotonergic 5-HT_1A receptors.

Original language	English
Pages (from-to)	38-43
Number of pages	6
Journal	Journal of Enzyme Inhibition and Medicinal Chemistry
Volume	25
Issue number	1
DOIs	https://doi.org/10.3109/14756360902932784
State	Published - Feb 2010

Bibliographical note

Funding Information:
This work was supported by Ewha Global Challenge (BK21), a KFDA grant (2008), and a Korean Research Foundation Grant funded by the Korean Government (MOEHRD) (KRF-2006-312-C00267), the Republic of Korea. Two of the authors (D.M. and Y.L.) appreciate the fellowship of the BK21 program from the Ministry of Education and Human Resources Development. The first two authors (J.-C.J. and D.M.) contributed equally to this work.

Keywords

3,4,5-trimethoxyphenyl acrylamides
Antinarcotic activity
Coupling synthesis
Morphine withdrawal syndrome
Wittig reaction

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10.3109/14756360902932784

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title = "Design, synthesis, and biological evaluation of 3,4,5-trimethoxyphenyl acrylamides as antinarcotic agents",

abstract = "The synthesis and biological evaluation of 3,4,5-trimethoxyphenyl acrylamides 1af as novel antinarcotic agents are described. The molecules were prepared by the Wittig reaction, followed by a coupling reaction between 3,4,5-trimethoxycinnamic acid (9) and aliphatic amines, which resulted in good yields. When tested for biological activity, compounds 1df exhibited strong inhibitory effects on the morphine withdrawal syndrome in mice due to their high binding affinities with serotonergic 5-HT1A receptors.",

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author = "Jung, {Jae Chul} and Dongguk Min and Heejeong Kim and Soyong Jang and Yongnam Lee and Wookyu Park and Khan, {Ikhlas A.} and Moon, {Hyung In} and Mankil Jung and Seikwan Oh",

note = "Funding Information: This work was supported by Ewha Global Challenge (BK21), a KFDA grant (2008), and a Korean Research Foundation Grant funded by the Korean Government (MOEHRD) (KRF-2006-312-C00267), the Republic of Korea. Two of the authors (D.M. and Y.L.) appreciate the fellowship of the BK21 program from the Ministry of Education and Human Resources Development. The first two authors (J.-C.J. and D.M.) contributed equally to this work.",

year = "2010",

month = feb,

doi = "10.3109/14756360902932784",

language = "English",

volume = "25",

pages = "38--43",

journal = "Journal of Enzyme Inhibition and Medicinal Chemistry",

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T1 - Design, synthesis, and biological evaluation of 3,4,5-trimethoxyphenyl acrylamides as antinarcotic agents

AU - Jung, Jae Chul

AU - Min, Dongguk

AU - Kim, Heejeong

AU - Jang, Soyong

AU - Lee, Yongnam

AU - Park, Wookyu

AU - Khan, Ikhlas A.

AU - Moon, Hyung In

AU - Jung, Mankil

AU - Oh, Seikwan

N1 - Funding Information: This work was supported by Ewha Global Challenge (BK21), a KFDA grant (2008), and a Korean Research Foundation Grant funded by the Korean Government (MOEHRD) (KRF-2006-312-C00267), the Republic of Korea. Two of the authors (D.M. and Y.L.) appreciate the fellowship of the BK21 program from the Ministry of Education and Human Resources Development. The first two authors (J.-C.J. and D.M.) contributed equally to this work.

PY - 2010/2

Y1 - 2010/2

N2 - The synthesis and biological evaluation of 3,4,5-trimethoxyphenyl acrylamides 1af as novel antinarcotic agents are described. The molecules were prepared by the Wittig reaction, followed by a coupling reaction between 3,4,5-trimethoxycinnamic acid (9) and aliphatic amines, which resulted in good yields. When tested for biological activity, compounds 1df exhibited strong inhibitory effects on the morphine withdrawal syndrome in mice due to their high binding affinities with serotonergic 5-HT1A receptors.

AB - The synthesis and biological evaluation of 3,4,5-trimethoxyphenyl acrylamides 1af as novel antinarcotic agents are described. The molecules were prepared by the Wittig reaction, followed by a coupling reaction between 3,4,5-trimethoxycinnamic acid (9) and aliphatic amines, which resulted in good yields. When tested for biological activity, compounds 1df exhibited strong inhibitory effects on the morphine withdrawal syndrome in mice due to their high binding affinities with serotonergic 5-HT1A receptors.

KW - 3,4,5-trimethoxyphenyl acrylamides

KW - Antinarcotic activity

KW - Coupling synthesis

KW - Morphine withdrawal syndrome

KW - Wittig reaction

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ER -

Design, synthesis, and biological evaluation of 3,4,5-trimethoxyphenyl acrylamides as antinarcotic agents

Abstract

Bibliographical note

Keywords

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