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The Synthesis of Novel GABA Uptake Inhibitors. 1. Elucidation of the Structure-Activity Studies Leading to the Choice of (R)-1-[4,4-bis(3-methyl-2-thienyl)-3-butenyl]-3-piperidinecarboxylic Acid (Tiagabine) as an Anticonvulsant Drug Candidate

The Synthesis of Novel GABA Uptake Inhibitors. 1. Elucidation of the Structure-Activity Studies Leading to the Choice of (R)-1-[4,4-bis(3-methyl-2-thienyl)-3-butenyl]-3-piperidinecarboxylic Acid (Tiagabine) as an Anticonvulsant Drug Candidate

K E Andersen, C Braestrup, F C Grønwald, A S Jørgensen, E B Nielsen, U Sonnewald, P O Sørensen, P D Suzdak, L J Knutsen

J Med Chem. 1993 Jun 11;36(12):1716-25.

PMID: 8510100

Abstract:

A series of different synthetic approaches to novel GABA uptake inhibitors are described, leading to examples which are derivatives of nipecotic acid and guvacine, substituted at nitrogen by 4,4-diaryl-3-butenyl or 2-(diphenylmethoxy)ethyl moieties. The in vitro value for inhibition of [3H]-GABA uptake in rat synaptosomes was determined for each compound. It was found that the most potent examples are those having a substituent in an "ortho" position in one or both aromatic/heteroaromatic groups. The majority of the compounds described are structurally related to tiagabine, (R)-1-[4,4-bis(3-methyl-2-thienyl)-3-butenyl]-3- piperidinecarboxylic acid hydrochloride (NNC 05-0328) and some of the reasoning behind the selection of this compound as a drug candidate is summarized.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP145821609	Tiagabine Related Compound A		145821-60-9	Price

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