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Synthesis, Modification, and Anticonvulsant Activity of 3′‐R 1 ‐Spiro[indoline‐3,6′‐[1,2,4]triazino[2,3 ‐c ]quinazolin]‐2,2′(7′ H )‐diones Derivatives
Author(s) -
Voskoboynik Oleksii Y.,
Kolomoets Oleksandra S.,
Nosulenko Inna S.,
Berest Galina G.,
Bilyi Andrii K.,
Karpenko Oleksandr V.,
Belenichev Igor F.,
Kovalenko Sergiy I.
Publication year - 2019
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3541
Subject(s) - indoline , isatin , chemistry , tautomer , alkylation , stereochemistry , medicinal chemistry , anticonvulsant , quinazoline , organic chemistry , epilepsy , neuroscience , biology , catalysis
Previously unknown 3′‐R 1 ‐5‐R 2 ‐spiro[indoline‐3,6′‐[1,2,4]triazino[2,3‐ c ]quinazoline]‐2,2′‐(7′ H )‐diones and their N‐substituted analogues were obtained via reaction of 6‐R 1 ‐3‐(2‐aminophenyl)‐1,2,4‐triazin‐5‐ones with isatin and its substituted derivatives. It was shown that alkylation of 3′‐R 1 ‐5‐R 2 ‐spiro[indoline‐3,6′‐[1,2,4]triazino[2,3‐ c ]quinazolin]‐2,2′‐(7′ H )‐diones by N ‐R 3 ‐chloroacetamides or chloroacetonitrile in the presence of а base proceeds by N‐1 atom of isatin fragment. The spectral properties ( 1 H and 13 C NMR spectra) of synthesized compounds were studied, and features of spectral patterns were discussed. The high‐effective anticonvulsant and radical scavenging agents among 3′‐R 1 ‐5‐R 2 ‐spiro[indoline‐3,6′‐[1,2,4]triazino[2,3‐ c ]quinazolin]‐2,2′(7′ H )‐diones and their N‐substituted derivatives were detected. It was shown that compounds 2.2 , 2.8 , and 3.1 exceed or compete the activity of the most widely used in modern neurology drug—lamotrigine on the pentylenetetrazole‐induced seizures model. The aforementioned fact may be considered as a reason for further profound study of synthesized compounds using other pathology models.