RESUMO
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.
Assuntos
Anti-Inflamatórios não Esteroides/síntese química , Anti-Inflamatórios não Esteroides/farmacologia , Pirimidinas/síntese química , Pirimidinas/farmacologia , Algoritmos , Animais , Animais Endogâmicos , Anti-Inflamatórios não Esteroides/química , Modelos Animais de Doenças , Edema/induzido quimicamente , Edema/tratamento farmacológico , Edema/prevenção & controle , Pé/patologia , Camundongos , Fosfolipases A2/metabolismo , Prostaglandina-Endoperóxido Sintases/metabolismo , Pirimidinas/química , Ratos , Úlcera/etiologiaRESUMO
Fries rearrangement of substituted phenyl benzoates 1a-j to substituted hydroxy benzophenones 2a-j was achieved in excellent yield. Further benzoylation of 2a-j to benzoyloxy benzophenones 4a-n, a benzophenone analogue was achieved in good yield. All the newly synthesized compounds were evaluated for their anti-inflammatory activity and were compared with standard drugs. Out of the compounds studied, the compounds 4c, 4e, 4g, 4h and 4k with chloro and methyl substituents at para position showed more potent activity than the standard drugs at all doses tested.
Assuntos
Anti-Inflamatórios não Esteroides/síntese química , Anti-Inflamatórios não Esteroides/farmacologia , Benzofenonas/síntese química , Benzofenonas/farmacologia , Animais , Anti-Inflamatórios não Esteroides/toxicidade , Benzofenonas/toxicidade , Carragenina , Cristalografia por Raios X , Inibidores de Ciclo-Oxigenase/síntese química , Inibidores de Ciclo-Oxigenase/farmacologia , Relação Dose-Resposta a Droga , Edema/induzido quimicamente , Edema/prevenção & controle , Dose Letal Mediana , Coelhos , Ratos , Úlcera Gástrica/induzido quimicamente , Úlcera Gástrica/patologiaRESUMO
Benzoylation of hydroxybenzophenones 1a-f affords substituted benzoyl phenyl benzoates 3a-f, which on Fries rearrangement using microwave irradiation led to a facile synthesis of solely dibenzoyl phenols 4a-f in excellent yield. The newly synthesized compounds were screened for their anti-inflammatory activity and were compared with standard drugs. Out of the compounds studied, the compound 4e showed more potent activity than the standard drugs at all doses tested.