RESUMO
The Friedel-Craft's acylation of 2,3-diphenyl-5-methylbenzofuran 1a with succinic anhydride gives beta-(2,3-diphenyl-5-methylbenzofuranoyl)propionic acid 1b. Acid 1b reacts with hydrazines yielding the corresponding tetrahydropyridazinones 2. 4,5-Dihydro-1,2-oxazin-6H-6-one 6 is formed by reaction of 1b with hydroxylamine hydrochloride. The reaction of the pyridazinone 2a with dialkyl sulfates, ethyl chloroacetate, Grignard reagents, amines in presence of formaldehyde (Mannich reaction), o-amino-phenol and thiourea has been investigated. The antimicrobial activities of compounds 1a-c, 2a-c, e, f, 4a, b and 5a, b as well as 7b are studied.
Assuntos
Anti-Infecciosos/síntese química , Benzofuranos/síntese química , Antibacterianos , Bactérias/efeitos dos fármacos , Benzofuranos/farmacologia , Fenômenos Químicos , Química , Fungos/efeitos dos fármacos , Testes de Sensibilidade MicrobianaRESUMO
Condensation of 5-formyl-6-methoxy-2,3-diphenylbenzofuran (I) and 6-formyl-5-methoxy-2,3-diphenylbenzofuran (II) with aliphatic or aromatic primary amines led to the formation of the corresponding anils (IIIa-k and IVa-c). The anils (IIIa,f,k or IVa-c) reacted with ethyl cyanoacetate, ethyl acetoacetate, or diethyl malonate to form the respective esters (Va-c or VIa-c). When Va-c or VIa-c were treated with pyridine hydrochloride, demethylation occurred followed by cyclization to form the corresponding furocoumarins (VIIa-c or VIIIa-c). Reduction of the anils using sodium borohydride furnished the corresponding Mannich bases (Xa-d and XI). The antimicrobial activity of compounds IIIi, IVc, Va, VIa, and VIIIa was investigated.
Assuntos
Benzofuranos/síntese química , Furocumarinas/síntese química , Antibacterianos , Anti-Infecciosos/síntese química , Bactérias/efeitos dos fármacos , Benzofuranos/farmacologia , Fenômenos Químicos , Físico-Química , Fungos/efeitos dos fármacos , Furocumarinas/farmacologia , Bases de Mannich/síntese química , Leveduras/efeitos dos fármacosRESUMO
The condensation of cinnamaldehyde, thienyl and furyl acrolein with dimethyl succinate in the presence of potassium tert-butoxide, gives the corresponding acid-esters (la-c) (R1 = Me) as major products. These esters are further converted into cyclopentadiene and cyclopentadienone derivatives. Dicondensation products (2a-c) are also obtained. Furthermore, the correlation between the chemical structures of the studied compounds and their respective biological activities were discussed.