Practical Synthesis, Antidepressant, and Anticonvulsant Activity of 3-Phenyliminoindolin-2-one Derivatives

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Abstract

Herein, a series of 3-phenyliminoindolin-2-one derivatives were designed, synthesized, and screened for their antidepressant and anticonvulsant activities. The IR spectra of the compounds afforded NH stretching (3340–3346 cm−1) bands and C=O stretching (1731–1746 cm−1). In the 1H-NMR spectra of the compounds, N-H protons of indoline ring were observed at 10.65–10.89 ppm generally as broad bands, and 13C-NMR spectra of the compounds C=O were seen at 161.72–169.27 ppm. Interestingly, compounds 3o, 3p and 3r significantly shortened immobility time in the The forced swimming test (FST) and The tail suspension test (TST) at 50 mg/kg dose levels. In addition, compound 3r exhibited higher levels of efficacy than the reference standard fluoxetine but had no effect on locomotor activity in the open-field test. Compound 3r significantly increased serotonin and norepinephrine and the metabolite 5-hydroxyindoleacetic acid in mouse brain, suggesting that the effects of compound 3r may be mediated through these neurotransmitters. In the seizure screen, 15 compounds showed some degree against PTZ-induced seizure at a dose of 100 mg/kg, and the tested compounds did not show any neurotoxicity at a dose of 300 mg/kg in the rotarod test.

A series of 3-phenyliminoindolin-2-one derivatives were synthesized and evaluated for their antidepressant and anticonvulsant activity. Compound 3r was found be to the most antidepressant-like activity. The probable mechanism of action of compound 3r is thought to be related to the increase in 5-HT and NE in the CNS. Fifteen compounds possessed anticonvulsant activity against PTZ-induced seizure.

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