A New Synthesis Method and GABA Transporters Inhibitory Activities of Tiagabine and Its Analogues

Chemical Research in Chinese Universities ›› 2006, Vol. 22 ›› Issue (3): 351-355.

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A New Synthesis Method and GABA Transporters Inhibitory Activities of Tiagabine and Its Analogues

ZHANG Jian-ge¹, JIANG Chang-sheng², ZHENG Jian-bin¹, WEN Ren¹, LIN Guo-qiang²

1. Department of Medicinal Chemistry, School of Pharmacy, Fudan University, Shanghai 200032, P. R. China;
2. Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 201203, P. R. China

Received:2005-04-19 Online:2006-06-24 Published:2011-08-06
Supported by:
Supported by the Science and Technology Commission of Shanghai Municipality(No. 03DZ19201).

Abstract

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 N-alkylation with (R)-3-piperidinecarboxylate. The resulting N-diheterocyclylalkenylpiperidine-3-carboxylic acid ester 11a-11e were saponified and then acidified toget the target compounds 1a-1e. The preliminary bioassays show that compound 1a-1e exhibited excellent inhibition of [³H]-GABA uptake in vitro of culture cells.

Key words: Tiagabine, Analogue, Synthesis, GABA transporter inhibitor

ZHANG Jian-ge, JIANG Chang-sheng, ZHENG Jian-bin, WEN Ren, LIN Guo-qiang. A New Synthesis Method and GABA Transporters Inhibitory Activities of Tiagabine and Its Analogues[J]. Chemical Research in Chinese Universities, 2006, 22(3): 351-355.

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A New Synthesis Method and GABA Transporters Inhibitory Activities of Tiagabine and Its Analogues

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