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Pharmaceuticals 2016, 9(2), 32; doi:10.3390/ph9020032

Synthesis and Pharmacological Properties of Novel Esters Based on Monocyclic Terpenes and GABA

Department of Pharmaceutical Chemistry, I.I. Mechnikov Odessa National University, Odessa 65026, Ukraine
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Author to whom correspondence should be addressed.
Academic Editor: Jean Jacques Vanden Eynde
Received: 29 April 2016 / Revised: 3 June 2016 / Accepted: 7 June 2016 / Published: 13 June 2016
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Abstract

Novel esters of γ-aminobutyric acid (GABA) with monocyclic terpenes were synthesized via Steglich esterification and characterized by 1H-NMR, IR and mass spectral studies. Their anticonvulsant, analgesic and anti-inflammatory activities were evaluated by a PTZ-induced convulsion model, AITC-induced hyperalgesia and AITC-induced paw edema, respectively. All studied esters, as well as their parent terpenes, were found to produce antinociceptive effects in the AITC-induced model and attenuate acute pain more than the reference drug benzocaine after their topical application. GABA esters of l-menthol and thymol were also shown to exceed the reference drug ibuprofen in their ability to decrease the inflammatory state induced by intraplantar injection of the TRPA1 activator AITC. The present findings indicate that GABA esters of carvacrol and guaiacol are not a classical prodrug and possess their own pharmacological activity. Prolonged antiseizure action of the ester based on the amino acid and guaiacol (200 mg/kg) was revealed at 24 h after oral administration. Furthermore, orally co-administered gidazepam (1 mg/kg) and GABA esters of l-menthol, thymol and carvacrol produce synergistic seizure prevention effects. View Full-Text
Keywords: TRP channels; terpene esters; GABA; anticonvulsant activity; analgesic effect; anti-inflammatory action; co-administration TRP channels; terpene esters; GABA; anticonvulsant activity; analgesic effect; anti-inflammatory action; co-administration
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Nesterkina, M.; Kravchenko, I. Synthesis and Pharmacological Properties of Novel Esters Based on Monocyclic Terpenes and GABA. Pharmaceuticals 2016, 9, 32.

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