RESUMO
A variety of novel 2-methylthio-3-substituted-5,6,7,8-tetrahydrobenzo (b) thieno[2,3-d]pyrimidin-4(3H)-ones have been synthesized by reacting (2-methylthio-4-oxo-3H-5,6,7,8-tetrahydrobenzo (b) thieno[2,3-d]pyrimidin-3-yl)dithiocarbamic acid methyl ester (5) with a variety of amines. The starting material dithiocarbamate (5) was synthesized from 2-amino-3-carbethoxy-4,5,6,7-tetrahydrobenzo (b) thiophene (1) by a novel innovative route. The title compounds were investigated for analgesic, anti-inflammatory, ulcerogenicity index and antibacterial activities. While the test compounds exhibited significant activity, the compounds 1-methyl-3-(2-methylthio-4-oxo-3H-5,6,7,8-tetrahydrobenzo (b) thieno[2,3-d]pyrimidin-3-yl)thiourea (A1), 1-dimethyl-3-(2-methylthio-4-oxo-3H-5,6,7,8-tetrahydrobenzo (b) thieno[2,3-d]pyrimidin-3-yl)thiourea (A2), 1-diethyl-3-(2-methylthio-4-oxo-3H-5,6,7,8-tetrahydrobenzo (b) thieno[2,3-d]pyrimidin-3-yl)thiourea (A3) and 1-pyrrolidinyl-3-(2-methylthio-4-oxo-3H-5,6,7,8-tetrahydrobenzo (b) thieno[2,3-d]pyrimidin-3-yl)thiourea (A4) showed more potent analgesic activity and the compounds 1-dimethyl-3-(2-methylthio-4-oxo-3H-5,6,7,8-tetrahydrobenzo (b) thieno[2,3-d]pyrimidin-3-yl)thiourea (A2), 1-diethyl-3-(2-methylthio-4-oxo-3H-5,6,7,8-tetrahydrobenzo (b) thieno-[2,3-d]pyrimidin-3-yl)thiourea (A3) and 1-pyrrolidinyl-3-(2-methylthio-4-oxo-3H-5,6,7,8-tetrahydrobenzo (b) thieno[2,3-d] pyrimidin-3-yl)thiourea (A4) showed more potent anti-inflammatory activity than the reference standard diclofenac sodium.
Assuntos
Analgésicos/síntese química , Antibacterianos/síntese química , Anti-Inflamatórios não Esteroides/síntese química , Pirimidinonas/síntese química , Pirimidinonas/farmacologia , Analgésicos/química , Analgésicos/farmacologia , Animais , Antibacterianos/química , Antibacterianos/farmacologia , Anti-Inflamatórios não Esteroides/química , Anti-Inflamatórios não Esteroides/farmacologia , Edema/tratamento farmacológico , Feminino , Espectroscopia de Ressonância Magnética , Masculino , Espectrometria de Massas , Camundongos , Testes de Sensibilidade Microbiana , Pirimidinonas/química , Ratos , Ratos Wistar , Espectroscopia de Infravermelho com Transformada de Fourier , Úlcera Gástrica/induzido quimicamenteRESUMO
A series of novel 2-substituted quinazolin-4(3H)-ones have been synthesized by condensing the aromatic primary amine of 2-substituted quinazolines with different aldehydes and ketones. The synthesized compounds were confirmed by their spectral data (IR, NMR and MS) and the purity was ascertained by elemental analysis. When these compounds were evaluated for analgesic and antiinflammatory activities, compounds I-VIII exhibited more potent analgesic activity than diclofenac sodium, while the compounds IV, V, VI and VII exhibited more potent antiinflammatory activity than diclofenac sodium. The activity values were found to be significant as compared to those of controls.