Synthesis and Anticonvulsant and Antidepressant Activity of Some 2-(6-bromo-2,3-dioxoindolin)-N-substituted Phenylacetamide Derivatives

Xie, Conghua; Tang, Lingling; Pan, Cheng-Yan; Guan, Linting

doi:10.1055/s-0034-1371870

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“…Briefly, the starting material amine reacted with chloral hydrate and sodium sulfate to yield the intermediate 1 . Then, compound 1 was stirred with concentrated sulfuric acid to give compound 2 according to methods previously described in the literature . 3‐phenyliminoindolin‐2‐one derivatives ( 3a – 3r ) were obtained by a nucleophilic addition–elimination reaction of substituted aniline with compound 2 .…”

Section: Resultsmentioning

confidence: 99%

“…After standing for about one and half an hour, the isatin is filtered with suction, washed several times with cold water to remove the sulfuric acid, and then dried by infrared. This product is pure enough for the next reaction .…”

Section: Methodsmentioning

confidence: 99%

“…During the heating period, some crystals of compound 1 separate. Cooled the solution in running water and the remainder crystallizes was filtered with suction and then dried in infrared drying oven .…”

Section: Methodsmentioning

confidence: 99%

“…Isatin derivatives also displayed as potent antidepressants activities and possess CNS‐monoamine oxidase (MAO) inhibition . A previous study from our laboratory found that isatin‐1‐ N ‐phenylacetamide derivatives and 2‐(6‐bromo‐2,3‐dioxoindolin)‐ N ‐substituted phenylacetamide derivatives showed the potent antidepressant‐like and anticonvulsant activity against maximal electroshock test and chemical‐induced substances PTZ . As part of our continuous efforts in this area, we recently embarked on a program to combine isatin and phenylamine through the preparation of a hybrid molecule composed on the two individual units (Figure ).…”

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

Quan

Jin

et al. 2015

Chem Biol Drug Des

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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 (1)H-NMR spectra of the compounds, N-H protons of indoline ring were observed at 10.65-10.89 ppm generally as broad bands, and (13)C-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.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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confidence: 99%

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