Association of Aurothiocarboxy Acids and Their Salts

Moore, E.E.; Ohman, R.J.; March, Bernice

doi:10.1002/jps.3030400403

Cited by 4 publications

(1 citation statement)

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“…The isothiouronium compounds were prepared either by reaction of thiourea on the corresponding whaloacids (Moore & Rappola, 1947), trans-3-chloro-2-propenoic acid (Kataev et al, 1969), or by acid catalysed addition of thiourea to propiolic acid (Kataev et al, 1969) (Moore & Rappola, 1947)…”

Section: Preparation Of Gaba Analoguesmentioning

confidence: 99%

Isothiouronium compounds as γ‐aminobutyric acid agonists

Allan

Dickenson

Hiern

et al. 1986

British J Pharmacology

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Analogues of γ‐aminobutyric acid (GABA) incorporating an isothiouronium salt as a replacement for a protonated amino functional group have been investigated for activity on: GABA receptors in the guinea‐pig ileum; [3H]‐GABA and [3H]‐diazepam binding to rat brain membranes; and GABA uptake and transamination. For the homologous series of α‐isothiouronium alkanoic acids, maximum GABA‐mimetic activity was found at 3‐[(aminoiminomethyl)thio]propanoic acid. Introduction of unsaturation into this compound gave two isomeric conformationally restricted analogues. The trans isomer was inactive at GABA receptors while the cis compound ((Z)‐3‐[(aminoiminomethyl)thio]prop‐2‐enoic acid (ZAPA)) was more potent than muscimol and GABA as a GABA agonist with respect to low affinity GABA receptor sites. Both isomers were moderately potent at inhibiting the uptake of [3H]‐GABA into rat brain slices. Comparison of possible conformations of the two unsaturated isomers by interactive computer graphics modelling and comparison with muscimol has led to a plausible active conformation of ZAPA, which may be a selective and potent agonist for low affinity GABA binding sites.

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Section: Preparation Of Gaba Analoguesmentioning

confidence: 99%