Synthesis, Modification, and Anticonvulsant Activity of 3′-R1 - Spiro[indoline-3,6′-[1,2,4]triazino[2,3-c]quinazolin]-2,2′(7′H)-diones Derivatives

J. Heterocycl. Chem. 2019, 56 (5), 1605-1612

DOI: 10.1002/jhet.3541

Voskoboynik O.; Kolomoets O.; Nosulenko I.; Berest G.; Bilyi A.; Karpenko O.; Belenichev I.; Kovalenko S.

Previously unknown 3′‐R1‐5‐R2‐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‐R1‐3‐(2‐aminophenyl)‐1,2,4‐triazin‐5‐ones with isatin and its substituted derivatives. It was shown that alkylation of 3′‐R1‐5‐R2‐spiro[indoline‐3,6′‐[1,2,4]triazino[2,3‐c]quinazolin]‐2,2′‐(7′H)‐diones by N‐R3‐chloroacetamides or chloroacetonitrile in the presence of а base proceeds by N‐1 atom of isatin fragment. The spectral properties (1H and 13C NMR spectra) of synthesized compounds were studied, and features of spectral patterns were discussed. The high‐effective anticonvulsant and radical scavenging agents among 3′‐R1‐5‐R2‐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.

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


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