Synthesis and Evaluation of Anti-Epileptic Properties of New Phthalimide-4,5-Dihydrothiazole-Amide Derivatives

Rafiei, Leila Sadat Tabatabaei; Asadi, Mehdi; Hosseini, Faezeh Sadat; Amanlou, Arash; Biglar, Mahmood; Amanlou, Massoud

doi:10.1080/10406638.2020.1776345

Cited by 5 publications

(9 citation statements)

References 20 publications

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“…Due to its potent activity of thalidomide in these tests, many attempts were made to design analogs of thalidomide to treat seizures and epilepsy. Different analogs are designed and tested in animal models of epilepsy to evaluate their ability to confront seizures ( 14 15 16 34 ). Among them, N-arylphthalimide analogs are wieldy studied.…”

Section: Discussionmentioning

confidence: 99%

“…Among them, N-arylphthalimide analogs are wieldy studied. Some of them have shown an ability to hold against PTZ-induced seizures ( 34 ), N-aryl-4-(1,3-dioxoisoindolin-2-yl) benzamides ( 16 ), phthalimide (N-aryl-2-(1,3-dioxoisoindolin-2-yl)-3-phenylpropanamide derivatives ( 14 ), phthalimide-4,5-dihydrothiazole-amide ( 15 ) revealed an anti-epileptic effect in PTZ-induced seizure.…”

Section: Discussionmentioning

confidence: 99%

“…Lithium chloride (Sigma, St Louis, MO, USA), pilocarpine HCl (Sina Daru Pharmaceutical Company, Tehran, Iran), diazepam, and scopolamine butylbromide (Hyoscine N-butylbromide, ChemiDarou Company, Tehran, Iran) were used as received. Thalidomide and three previously synthesized thalidomide derivatives (compound 5B, N-(4-chlorophenyl)-2-((1, 3-dioxoisoindolin-2-yl) methyl)-4, 5-dihydrothiazole-4-carboxamide; compound 5C, 2-(1,3-dioxoisoindolin-2-yl)-N,3-diphenylpropanamide; and compound 5D, N-(3,4-dimethylphenyl)-4-(1, 3-dioxoisoindolin-2-yl)benzamide) were received as gifts from the Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences ( 14 15 16 ).…”

Section: Methodsmentioning

confidence: 99%

“…Considering the beneficial effects of thalidomide on refractory epilepsy as well as, the beneficial impact of this drug and related compounds in recent reports, the latest researches were designed with the intention to increase its anti-epileptic activity and reduce its main side effects ( 11 12 14 15 16 ).…”

Section: Introductionmentioning

confidence: 99%

“…In the present study, the anti-epileptic effects and histopathological evaluation of the three most potent phthalimide analogs of thalidomide (compounds 5B, 5C, and 5D) in which the glutarimide ring was replaced by non-aliphatic side chains were investigated employing the lithium-pilocarpine-induced status epilepticus model in rats and the results compared to previously reported anticonvulsive activity in the pentylenetetrazole (PTZ)-induced seizures model in mice ( 14 15 16 ).…”

Section: Introductionmentioning

confidence: 99%

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Anticonvulsive evaluation and histopathological survey of thalidomide synthetic analogs on lithium-pilocarpine-induced status epilepticus in rats

Amanlou

Eslami

Shayan

et al. 2021

Research in Pharmaceutical Sciences

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Background and purpose: Status epilepticus is a severe neurological disorder that can be life-threatening. Thalidomide and its analogs have shown promising results to confront pentylenetetrazole-induced seizures. This study aimed to evaluate the potential effects of three synthesized thalidomide derivatives on lithium-pilocarpine-induced status epilepticus. Experimental approach: To induce status epilepticus, rats received lithium chloride (127 mg/kg, i.p.) and pilocarpine HCl (60 mg/kg, i.p.) 20 h after lithium chloride injection. Thirty min before pilocarpine HCl administration, rats received hyoscine N-butyl bromide (1 mg/kg, i.p.) and concurrently one of the test compounds (5B, 5C, and 5D), diazepam, thalidomide, or vehicle (4% DMSO) to evaluate their anti-epileptic effects. Epileptic seizures scores were assessed through the Racine scale. Twenty-four h after injection of pilocarpine, brain samples were extracted for further histopathological evaluation. Findings/Results: Results revealed that among tested compounds (5B, 5C, and 5D), only compound 5C (1 mg/kg) exhibited excellent anti-epileptic activity comparable to diazepam (10 mg/kg). Compound 5D (100 mg/kg) only demonstrated comparable anti-epileptic activity to thalidomide (1 mg/kg). Compound 5B did not have any anti-epileptic activity even at the dose of 100 mg/kg. The histopathological survey showed that compound 5C has more neuroprotective effects than diazepam and thalidomide in the cortex of the brain. In the cornu ammonis 1 region, thalidomide had higher protective properties and in the cornu ammonis 3 and dentate gyrus areas, diazepam had higher efficacy to prevent necrosis. Conclusion and implications: Compound 5C is a good candidate for further studies regarding its potency, compared to thalidomide and diazepam.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Anticonvulsive evaluation and histopathological survey of thalidomide synthetic analogs on lithium-pilocarpine-induced status epilepticus in rats

Amanlou

Eslami

Shayan

et al. 2021

Research in Pharmaceutical Sciences

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Synthesis, Docking and Antiepileptic Activity of New 2-((1,5-Diphenyl-1H-1,2,4-Triazol-3-yl)Thio)-N-Phenylacetamide Derivatives

Amanlou

Nassireslami

Hosseini

et al. 2021

Polycyclic Aromatic Compounds

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Synthesis, carbonic anhydrase inhibition studies and modelling investigations of phthalimide–hydantoin hybrids

Abdoli,

Bonardi,

Gratteri

et al. 2024

Journal of Enzyme Inhibition and Medicinal Chemistry

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A novel series of hydantoins incorporating phthalimides has been synthesised by condensation of activated phthalimides with 1-aminohydantoin and investigated for their inhibitory activity against a panel of human (h) carbonic anhydrase (CA, EC 4.2.1.1): the cytosolic isoforms hCA I, hCA II, and hCA VII, secreted isoform hCA VI, and the transmembrane hCA IX, by a stopped-flow CO 2 hydrase assay. Although all newly developed compounds were totally inactive on hCA I and mainly ineffective towards hCA II, they generally exhibited moderate repressing effects on hCA VI, VII, and IX with K I s values in the submicromolar to micromolar ranges. The salts 3a and 3b , followed by derivative 5 , displayed the best inhibitory activity of all the evaluated compounds and their binding mode was proposed in silico . These compounds can also be considered interesting starting points for the development of novel pharmacophores for this class of enzyme inhibitors.

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Synthesis and Evaluation of Anti-Epileptic Properties of New Phthalimide-4,5-Dihydrothiazole-Amide Derivatives

Cited by 5 publications

References 20 publications

Anticonvulsive evaluation and histopathological survey of thalidomide synthetic analogs on lithium-pilocarpine-induced status epilepticus in rats

Anticonvulsive evaluation and histopathological survey of thalidomide synthetic analogs on lithium-pilocarpine-induced status epilepticus in rats

Synthesis, Docking and Antiepileptic Activity of New 2-((1,5-Diphenyl-1H-1,2,4-Triazol-3-yl)Thio)-N-Phenylacetamide Derivatives

Synthesis, carbonic anhydrase inhibition studies and modelling investigations of phthalimide–hydantoin hybrids

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