2-[(3-Aminoalkyl-(alkaryl-,aryl-))-1H-1,2,4-triazol-5-yl]anilines: synthesis and anticonvulsant activity

Yulya Martynenko; Galina Berest; Nina Bukhtiayrova; Igor Belenichev; Oleksiy Voskoboinik; Sergiy Kovalenko

doi:10.3906/kim-2002-24

2-[(3-Aminoalkyl-(alkaryl-,aryl-))-¹H-1,2,4-triazol-5-yl]anilines: synthesis and anticonvulsant activity

Turk J Chem. 2020 Jun 1;44(3):746-755. doi: 10.3906/kim-2002-24. eCollection 2020.

Authors

Yulya Martynenko¹, Galina Berest¹, Nina Bukhtiayrova², Igor Belenichev², Oleksiy Voskoboinik¹, Sergiy Kovalenko¹

Affiliations

¹ Department of Organic and Bioorganic Chemistry, Pharmaceutical Faculty, Zaporizhzhia State Medical University, Zaporizhzhia Ukraine.
² Department of Pharmacology and Medical Formulation, Pharmaceutical Faculty, Zaporizhzhia State Medical University, Zaporizhzhia Ukraine.

Abstract

The presented work is devoted to the development of synthesis methods for novel 2-[(3-aminoalkyl-(alkaryl-, aryl-))-1H-1,2,4-triazolo]anilines. Abovementioned compounds were obtained via hydrazinolysis (Ing-Manske procedure) and acid hydrolysis of corresponding N -acylated{([1,2,4]triazolo[1,5-c]quinazolin-2-yl)alkyl-(alkaryl-, aryl-)}amines. The regioselectivity of hydrazinolysis and hydrolysis were established. The features of spectral characteristics werestudied and discussed. Characteristic patterns of protons signals splitting in ¹H NMR of the synthesized compounds were established. The effect of the synthesized compounds on the pentylenetetrazol seizures was studied. It was found that according to some indicators, anticonvulsant activity of 2-[(3-aminoalkyl-(alkaryl-, aryl-))-1H-1,2,4-triazolo]anilines superior or comparable with effect of the reference drug "Lamotrigine". It is a valid argument for their further structural modification, in-depth study of activity mechanisms and further study of anticonvulsant activity on other experimental seizures models.

Keywords: 2-[(3-aminoalkyl-(alkaryl-,aryl-))-1H-1,2,4-triazolo]anilines; N -acylated{([1,2,4]triazolo[1,5-c]quinazolin-2-yl)alkyl-(alkaryl-, aryl-)}amines; acidic hydrolysis; anticonvulsant activity; hydrazinolysis.