A new synthesis method and GABA transporters inhibitory activities of Tiagabine and its analogues

Jian Ge Zhang; Chang Sheng Jiang; Jian Bin Zheng; Ren Wen; Guo Qiang Lin

doi:10.1016/S1005-9040(06)60114-1

A new synthesis method and GABA transporters inhibitory activities of Tiagabine and its analogues

Jian Ge Zhang^*, Chang Sheng Jiang, Jian Bin Zheng, Ren Wen, Guo Qiang Lin

^*Corresponding author for this work

Neurology

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

1 Scopus citations

Abstract

A new synthetic method and GABA transporter inhibitory activities of Tiagabine and its analogues are described. The key intermediates 4-tosyl-1,1-diaryl/heteroaryl-1-butene 10a-10e were synthesized by Wittig reaction, and followed by W-alkylation with (R)-3-piperidinecarboxylate. The resulting N-diheterocyclylalkenylpiperidine-3-carboxylic acid ester 11a-11e were saponified and then acidified to-get the target compounds 1a-1e. The preliminary bioassays show that compounds 1a-1e exhibited excellent inhibition of [³H]-GABA uptake in vitro of culture cells.

Original language	English (US)
Pages (from-to)	351-355
Number of pages	5
Journal	Chemical Research in Chinese Universities
Volume	22
Issue number	3
DOIs	https://doi.org/10.1016/S1005-9040(06)60114-1
State	Published - May 2006

Keywords

Analogue
GABA transporter inhibitor
Synthesis
Tiagabine

ASJC Scopus subject areas

General Chemistry

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10.1016/S1005-9040(06)60114-1

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title = "A new synthesis method and GABA transporters inhibitory activities of Tiagabine and its analogues",

abstract = "A new synthetic method and GABA transporter inhibitory activities of Tiagabine and its analogues are described. The key intermediates 4-tosyl-1,1-diaryl/heteroaryl-1-butene 10a-10e were synthesized by Wittig reaction, and followed by W-alkylation with (R)-3-piperidinecarboxylate. The resulting N-diheterocyclylalkenylpiperidine-3-carboxylic acid ester 11a-11e were saponified and then acidified to-get the target compounds 1a-1e. The preliminary bioassays show that compounds 1a-1e exhibited excellent inhibition of [3H]-GABA uptake in vitro of culture cells.",

keywords = "Analogue, GABA transporter inhibitor, Synthesis, Tiagabine",

author = "Zhang, {Jian Ge} and Jiang, {Chang Sheng} and Zheng, {Jian Bin} and Ren Wen and Lin, {Guo Qiang}",

note = "Funding Information: * Supported by the Science and Technology Commission of Shanghtu Municipality( No. 03DZ19201) .",

year = "2006",

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doi = "10.1016/S1005-9040(06)60114-1",

language = "English (US)",

volume = "22",

pages = "351--355",

journal = "Chemical Research in Chinese Universities",

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publisher = "Jilin University Press",

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TY - JOUR

T1 - A new synthesis method and GABA transporters inhibitory activities of Tiagabine and its analogues

AU - Zhang, Jian Ge

AU - Jiang, Chang Sheng

AU - Zheng, Jian Bin

AU - Wen, Ren

AU - Lin, Guo Qiang

N1 - Funding Information: * Supported by the Science and Technology Commission of Shanghtu Municipality( No. 03DZ19201) .

PY - 2006/5

Y1 - 2006/5

N2 - A new synthetic method and GABA transporter inhibitory activities of Tiagabine and its analogues are described. The key intermediates 4-tosyl-1,1-diaryl/heteroaryl-1-butene 10a-10e were synthesized by Wittig reaction, and followed by W-alkylation with (R)-3-piperidinecarboxylate. The resulting N-diheterocyclylalkenylpiperidine-3-carboxylic acid ester 11a-11e were saponified and then acidified to-get the target compounds 1a-1e. The preliminary bioassays show that compounds 1a-1e exhibited excellent inhibition of [3H]-GABA uptake in vitro of culture cells.

AB - A new synthetic method and GABA transporter inhibitory activities of Tiagabine and its analogues are described. The key intermediates 4-tosyl-1,1-diaryl/heteroaryl-1-butene 10a-10e were synthesized by Wittig reaction, and followed by W-alkylation with (R)-3-piperidinecarboxylate. The resulting N-diheterocyclylalkenylpiperidine-3-carboxylic acid ester 11a-11e were saponified and then acidified to-get the target compounds 1a-1e. The preliminary bioassays show that compounds 1a-1e exhibited excellent inhibition of [3H]-GABA uptake in vitro of culture cells.

KW - Analogue

KW - GABA transporter inhibitor

KW - Synthesis

KW - Tiagabine

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DO - 10.1016/S1005-9040(06)60114-1

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SN - 1005-9040

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JO - Chemical Research in Chinese Universities

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A new synthesis method and GABA transporters inhibitory activities of Tiagabine and its analogues

Abstract

Keywords

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