RESUMO
In the present investigation, a series of novel {5-chloro-2-[(3-(substitutedphenyl)-1,2,4-oxadiazol-5-yl)-methoxy]-phenyl}-(phenyl)-methanones (3a-i) have been synthesized from 5-(chloromethyl)-3-substitutedphenyl-1,2,4-oxadiazole (2a-i). The newly synthesized compounds were characterized by IR, NMR (1H and 13C), mass spectral and elemental analysis. The title compounds were investigated for in-vitro qualitative (zone of inhibition) and quantitative (MIC) antibacterial activity by agar cup plate and microtitration methods, respectively. The minimum inhibitory concentration and structure activity relationships (SARs) were evaluated. Amongst the synthesized compounds in this series, {5-chloro-2-[(3-(2,5-difluoro-4-methyl-phenyl)-1,2,4-oxadiazol-5-yl)-methoxy]-phenyl}-(phenyl)-methanone (3d) was found to exhibit significant activity with MICs of 21.5, 22.4, 29.8 and 30.6 microg/mL against Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Klebsiella pneumoniae, respectively.
Assuntos
Antibacterianos/síntese química , Antibacterianos/farmacologia , Benzofenonas/síntese química , Benzofenonas/farmacologia , Desenho de Fármacos , Antibacterianos/química , Bactérias/efeitos dos fármacos , Benzofenonas/química , Espectroscopia de Ressonância MagnéticaRESUMO
A series of 2-[2-(aroyl-aroxy)-methyl]-4-phenyl-1,3-thiazoles 4a-j were obtained via multiple step synthesis sequence beginning with the hydroxybenzophenones (1a-g). Hydroxybenzophenones on reaction with chloroacetonitrile affords [(2-benzoyl) phenoxy] acetonitrile (2a-g), which reacts with H(2)S/NH(4)OH and yields [(2-benzoyl) phenoxy] acetothiamide (3a-g), which on treatment with phenacylbromides affords 2-[2-(aroyl-aroxy)-methyl]-4-phenyl-1,3-thiazoles (4a-j). All the newly synthesized compounds were evaluated for their anti-inflammatory activity and were compared with standard drugs. Of the compounds studied, (4g), compounds with chloro substituents showed more potent activity than the standard drug phenyl butazone at all doses tested.
Assuntos
Anti-Inflamatórios/síntese química , Tiazóis/química , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/uso terapêutico , Benzofenonas/química , Edema/tratamento farmacológico , Ratos , Tiazóis/síntese química , Tiazóis/uso terapêutico , Testes de ToxicidadeRESUMO
Reaction of 6a-f individually with 2-methylsulfonyl-4,6-dimethoxypyrimidine yielded 7a-f in excellent yield. The newly synthesized heterocycles were characterized by IR, (1)H NMR, and mass spectral data. Compounds 7a-f was screened for their anti-inflammatory activity and were compared with standard drugs. Of the compounds studied, the compound 7e showed more potent activity than the standard drugs at all doses tested.
