RESUMEN
The hitherto unknown 2-isopropyl-6,8-dibromo-4H-3,1-benzoxazin-4-one (2) was subjected to condensation with either primary or secondary amines affording the benzamide derivatives (3-7), while with alcohols in presence of the base, corresponding esters were obtained (8 and 9). Acylation of the hydrazide (12) or its cyclized form (13) gave (14-17). The quinazolinone derivative (18) was obtained either when (12) was reacted with nitrous acid or via fusion of (2) with ammonium acetate. The thione (20) which was obtained via reaction of (18) with Lawesson's reagent, was subjected to either alkylation yielding (21-25) or desulphurization with primary amines affording (26 and 27). Treatment of (18) as well as (20) with a chlorinating agent provided (29, 30) and (28, 29) mixtures, respectively. Ten of our compounds were examined against Sclerotium cepivorum as well as Botrytis allii on PDA media. These compounds showed a significant reduction of mycelial growth and scleratia number of these fungi which cause the white rot and neck rot diseases of onion.
Asunto(s)
Basidiomycota/efectos de los fármacos , Botrytis/efectos de los fármacos , Fungicidas Industriales/síntesis química , Oxazinas/síntesis química , Quinazolinas/síntesis química , Fungicidas Industriales/química , Fungicidas Industriales/farmacología , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Cebollas/microbiología , Oxazinas/química , Oxazinas/farmacología , Quinazolinas/química , Quinazolinas/farmacología , Relación Estructura-ActividadRESUMEN
The hitherto unknown bis[quinazolin-4-one-2-yl]-m-phenylene (2d), and its 3-N-substituted derivatives were prepared from the corresponding bis[3,1-benzoxazin-4-one-2-yl]-m-phenylene (1) as precursor. The quinazolinone derivative 2d was converted into bis[quinazolin-4-thioxo-2-yl]-m-phenylene (3) via different routes, bis[4-chloroquinazolin-2-yl]-m-phenylene (8) and bis[4-hydrazinoquinazolin-2-yl]-m-phenylene (11), respectively. The structures of the compounds 2, 3, 8, and 11 were supported by elemental, spectroscopic analysis as well as, chemical proofs. Biological activities of some of the produced compounds were evaluated.
Asunto(s)
Antiinfecciosos/síntesis química , Quinazolinas/síntesis química , Antibacterianos , Antiinfecciosos/farmacología , Antifúngicos/síntesis química , Antifúngicos/farmacología , Bacterias/efectos de los fármacos , Hongos/efectos de los fármacos , Espectroscopía de Resonancia Magnética , Pruebas de Sensibilidad Microbiana , Quinazolinas/farmacología , Espectrofotometría InfrarrojaRESUMEN
The design of new heterocyclic derivatives as modulatory agents at EAA receptors is described. In particular, the potent and selective activity at the NMDA receptor of trans-4-hydroxypipecolic acid-4-sulfate, as well as the neuroprotective properties of substituted thiokynurenates, a new class of competitive antagonists at the glycine site of the NMDA receptor complex, are reported.
