Design, synthesis and pharmacological profile of (−)-verbenone hydrazones

Author:

Nesterkina Mariia1,Barbalat Dmytro2,Kravchenko Iryna1

Affiliation:

1. Department of Organic and Pharmaceutical Technologies, Odessa National Polytechnic University, Odessa 65044, Ukraine

2. Department of Analytical and Toxicological Chemistry, Odessa I.I. Mechnikov National University, Odessa 65082, Ukraine

Abstract

AbstractA series of novel (−)-verbenone hydrazones was designed and synthesized via condensation of terpenoid with hydrazides derived from phenoxyacetic acid. The structure of target compounds was confirmed by 1H-NMR and 13C-NMR analysis, Raman and FT-IR spectroscopy, electrospray ionization method and fast atom bombardment (FAB) mass spectrometry. Thermal properties of (−)-verbenone hydrazones 3a3e were estimated by differential scanning calorimetry and their purity by HPLC coupled to mass spectrometry. Verbenone hydrazones were revealed to exist as Z/E geometrical isomers about C═N bond and cis/trans amide conformers. Verbenone derivatives were estimated as potential anticonvulsant agents after their oral administration against pentylenetetrazole and maximal electroshock-induced seizures in mice. Analgesic effect of hydrazones was studied by topical application on models of allyl isothiocyanate and capsaicin-induced pain. The present findings indicate that verbenone hydrazones contribute to seizure protection both at short (6 h) and long (24 h) time periods by blocking chemical- and electroshock-induced convulsions. Binding of compounds 3a3e to TRPA1/TRPV1 ion channels was suggested as a feasible mechanism explaining their significant analgesic activity.

Publisher

Walter de Gruyter GmbH

Subject

Materials Chemistry,General Chemistry

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