Efficient synthesis of the GABAA receptor agonist trans-4-aminocrotonic acid (TACA)

Sean G Forrester; Joshua Foster; Sebastien Robert; Lidya Salim; Jean-Paul Desaulniers

doi:10.1016/j.bmcl.2017.07.050

Efficient synthesis of the GABA_A receptor agonist trans-4-aminocrotonic acid (TACA)

Bioorg Med Chem Lett. 2017 Sep 15;27(18):4512-4513. doi: 10.1016/j.bmcl.2017.07.050. Epub 2017 Jul 20.

Authors

Sean G Forrester¹, Joshua Foster¹, Sebastien Robert¹, Lidya Salim¹, Jean-Paul Desaulniers²

Affiliations

¹ Faculty of Science, University of Ontario Institute of Technology, Oshawa, ON L1H 7K4, Canada.
² Faculty of Science, University of Ontario Institute of Technology, Oshawa, ON L1H 7K4, Canada. Electronic address: jean-paul.desaulniers@uoit.ca.

PMID: 28838689
DOI: 10.1016/j.bmcl.2017.07.050

Abstract

Investigations into the pharmacology of different types of cys-loop GABA receptor have relied for years on the chemical modification of GABA-like compounds. The GABA metabolite GABOB is an attractive molecule to modify due to its convenient chemical structure. In the process of developing new GABA-mimic compounds from GABOB as a starting compound three small molecule GABA derivatives were synthesized using a variety of chemical transformations. Amongst these, a new and reliable method to synthesize TACA (trans-4-aminocrotonic acid) is reported.

Keywords: GABA; GABA(A) receptor; GABOB; H. contortus; TACA.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Crotonates / chemical synthesis
Crotonates / chemistry
Crotonates / pharmacology*
Dose-Response Relationship, Drug
GABA-A Receptor Agonists / chemical synthesis
GABA-A Receptor Agonists / chemistry
GABA-A Receptor Agonists / pharmacology*
Molecular Structure
Oocytes / drug effects
Receptors, GABA-A / metabolism*
Structure-Activity Relationship
Xenopus laevis

Substances

Crotonates
GABA-A Receptor Agonists
Receptors, GABA-A
4-aminocrotonic acid