Synthesis and biological evaluation of some new quinazolin-4(3H)-ones derivatives as anticonvulsants

Deepak Gupta, Rajiv Kumar, Ram Kumar Roy, Adish Sharma, Israr Ali, Mohammad Shamsuzzaman

Research output: Contribution to journalJournal articlepeer-review

12 Scopus citations

Abstract

Epilepsy is the most common neurological disorder known, affecting around 1 % of the world's population, characterized by recurrent seizure attack. A new series of 2-phenyl-3-(3-(substituted-benzylideneamino)-quinazolin-4(3H)-one derivatives (6a-h) was synthesized through condensation of anthranilic acid (1) and benzoyl chloride to give 2-phenyl-benzo[d][1,3]oxazin-4-one (2). Compound 2 was refluxed with hydrazine hydrate and yielded intermediate 3. Further, the intermediate 3 was dehydrated with catalytic amount of GAA and yielded 3-amino-2-phenyl-1H-quinazolin-4-one (4). Compound 4 was further treated with 3-hydroxy benzaldehyde and small amount of GAA to afford schiff base derivative 5. Finally, the Schiff base was treated with various alkyl halide to provide desired compounds 6a-h and structures of the final compounds were confirmed on the basis of their FTIR, NMR, and Mass spectral data. Anticonvulsant activity was evaluated by the maximal electroshock test, further their minimum motor impairment and CNS depressant effect were evaluated by the rotorod motor impairment and Porsolt's force swim tests, respectively. The results showed that 2-phenyl-3-(3-(propoxybenzylideneamino)-3H-quinazolin-4-one (6c) is the most promising compound with the lowest side effects.

Original languageEnglish
Pages (from-to)3282-3288
Number of pages7
JournalMedicinal Chemistry Research
Volume22
Issue number7
DOIs
StatePublished - Jul 2013
Externally publishedYes

Keywords

  • CNS depressant
  • MES
  • Motor impairment
  • Quinazolin-4(3H)-one
  • Schiff base

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