Synthesis of Benzofuro[3,2‐<i>e</i>]‐1,4‐diazepines of Pharmacological Interest

Basavaraja, K. M.; Vaidya, V. P.; Chikkanna, Chandrashekhar

doi:10.1155/2008/920926

Cited by 7 publications

(3 citation statements)

References 10 publications

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“…TLC was used to monitor the completion of the reaction; the structures of products were assessed by interpretation of IR and NMR spectra obtained. The spectroscopic data of IR and 1 H-NMR are in agreement with the structure of fused 1, 4-diazepine derivatives 3,4,6,7,8,9,10 .…”

Section: Resultssupporting

confidence: 76%

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2011

IJPSR

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Section: Resultssupporting

confidence: 76%

Untitled

2011

IJPSR

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“…Purity of the compounds and the progress of reaction were checked by thin layer chromatography (TLC) on silica gel G plates (Qualigens, India) using cyclohexane/ethyl acetate (8:2) as a solvent system and the spots were located either under UV light or by exposure to iodine vapors. 3-amine (2b) and N-(2-benzoyl-benzofuran-3-yl)-2-chloroacetamide (3a) were prepared following the reported methods (12,16).…”

Section: Chemistrymentioning

confidence: 99%

“…These essential features are present in most popular anticonvulsant drugs such as phenytoin, carbamazepine, phenobarbital and ralitoline. Benzofuran derivatives have diverse pharmacological activities, like anticonvulsant (12)(13)(14)(15), antiinflammatory (13), analgesic (16), antioxidant and antimicrobial (17,18), neuroprotective (19), anticancer, cytotoxic, inhibiting of NF-κB and protein kinase (20)(21)(22). Benzofuran, a versatile heterocyclic molecule possessing a preliminary anticonvulsant property, has been selected to explore as a hydrophobic functional group for the binding site.…”

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confidence: 99%

Design, synthesis and evaluation of benzofuran-acetamide scaffold as potential anticonvulsant agent

et al. 2016

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A series of N-(2-(benzoyl/4-chlorobenzoyl)-benzofuran- 3-yl)-2-(substituted)-acetamide derivatives (4a-l, 5a-l) was synthesized in good yield. All synthesized compounds were in agreement with elemental and spectral data. The anticonvulsant activity of all synthesized compounds was assessed against the maximal electroshock induced seizures (MES) model in mice. Neurotoxicity was evaluated using the rotarod method. The majority of compounds exhibited anticonvulsant activity at a dose of 30 mg kg-1 body mass during 0.5-4 h, indicating their ability to prevent seizure spread at low doses. Relative to phenytoin, [N-(2-(4-chlorobenzoyl)benzofuran-3-yl)-2-(cyclohexyl( methyl) amino)-acetamide] (5i) and [N-(2-(4-chlorobenzoyl)benzofuran-3-yl)-2-(4-methylpiperidin-1- yl)-acetamide] (5c) demonstrated comparable relative anticonvulsant potency of 0.74 and 0.72, respectively, whereas [(N-(2-(4-chlorobenzoyl)benzofuran-3-yl)-2-(4-(furan-2-carbonyl)-piperazin-1-yl)-acetamide] (5f) exhibited the lowest relative potency of 0.16. The ALD50 of tested compounds ranged from 1.604 to 1.675 mmol kg-1 body mass. The ED50 of synthesized compounds ranged from 0.055 to 0.259 mmol kg-1 (~23.4 to 127.6 mg kg-1) body mass. The pharmacophore mapping of the examined compounds on standard drugs (phenobarbital, phenytoin, ralitolin and carbamazepine) strongly suggests that these compounds may exert their anticonvulsant activity via the same established mechanism as that of known drugs.

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