Synthesis of 2-aryl-3-triazolyl-indoles from phenacyltriazole-derived hydrazones: Exploring new scaffolds for anticonvulsant activity

A novel series of 1-(2-(halophenyl)-2-(2-arylhydrazono)ethyl)-1H-1,2,4-triazoles 7a-l and their Fischer in-dolic products namely 2-(halophenyl)-3-(1H-1,2,4-triazol-1-yl)-1H-indoles 8a-l were synthesized conve-niently. Furthermore, the ( Z or E )-geometry of arylhydrazones was identified by 1 H NMR spectroscopy. The antiepileptic potential of both series of compounds was studied by PTZ and MES seizure models. Based on the obtained data, most of hydrazones showed significant protective effect on MES-induced seizure model. Among them, compounds 7a and 7h were demonstrated to be the most potent ones against MES-induced seizures with rapid-acting properties. Generally, the indolic compounds showed less activity when compared to their original arylhydrazones.(c) 2022 Elsevier B.V. All rights reserved.

Automated summary

A series of novel 1-(2-(halophenyl)-2-(2-arylhydrazono)ethyl)-1H-1,2,4-triazoles 7a-l and their Fischer indolic products 2-(halophenyl)-3-(1H-1,2,4-triazol-1-yl)-1H-indoles 8a-l were synthesized conveniently. The (Z or E) geometry of arylhydrazones was identified by 1H NMR spectroscopy. The antiepileptic potential of both series of compounds was evaluated using PTZ and MES seizure models. The majority of hydrazones exhibited significant protective effects against MES-induced seizures, with compounds 7a and 7h being the most potent and rapid-acting. Indolic compounds generally displayed lower activity compared to their original arylhydrazones.