Design and synthesis of 3-(4-ethylphenyl)-2-substituted amino-3H-quinazolin-4-ones as a novel class of analgesic and anti-inflammatory agents.

Medicinal Chemistry Research Laboratory, Dayananda Sagar College of Pharmacy, Kumaraswamy Layout, Bangalore, India.
Journal of Enzyme Inhibition and Medicinal Chemistry (Impact Factor: 1.5). 08/2008; 23(6):839-47. DOI: 10.1080/14756360701746229
Source: PubMed

ABSTRACT A new series of 3-(4-ethylphenyl)-2-substituted amino-3H-quinazolin-4-ones were synthesized by reacting the amino group of 2-hydrazino-3-(4-ethylphenyl)-3H-quinazolin-4-one from 4-ethyl aniline with a variety of aldehydes and ketones. The title compounds were investigated for analgesic, anti-inflammatory and ulcerogenic index activities. The compound 2-(N'-3-pentylidene-hydrazino)-3-(4-ethylphenyl)-3H-quinazolin-4-one (AS2) emerged as the most active compound of the series and was moderately more potent than the reference standard diclofenac sodium. Interestingly the test compounds showed only mild ulcerogenic potential when compared to aspirin.

  • [Show abstract] [Hide abstract]
    ABSTRACT: A series of 3-[(4-substituted-benzylidene)-amino]-2-phenyl-3H-quinazolin-4-ones (5a-k) were synthesized by reacting 3-amino-2-phenyl-1H-quinazolin-4-one with p-hydroxybenzaldehyde, and then further with various alkyl/benzyl halides or substituted phenacyl bromides. The structures of the compounds were confirmed on the basis of IR, NMR, MS and elemental analysis. Anticonvulsant activities were evaluated using the MES and scPTZ tests. Some of the selected compounds were evaluated for antidepressant activity by forced swim pool test. Compound 3-[(4-butoxy-benzylidene)-amino]-2-phenyl-3H-quinazolin-4-one was emerged as the most promising anticonvulsant agent without any motor impairment effect. The whole brain GABA estimation of brain homogenate indicated that the anticonvulsant activity of above mentioned quinazolinone derivatives might be due to an increased GABA concentration.
    Archives of Pharmacal Research 01/2013; · 1.54 Impact Factor
  • [Show abstract] [Hide abstract]
    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. Graphical abstract
    Medicinal Chemistry Research 22(7). · 1.61 Impact Factor
  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: This review article aims at providing recent developments in synthetic methodologies to access quinazoline and quinazolinone scaffolds with their diverse array of potential biological applications.
    European Journal of Medicinal Chemistry 06/2014; 76:193–244. · 3.43 Impact Factor