RESUMEN
The condensation of 1,5-diphenylpyrrolidine-2,4-dione (1) with ethyl orthoformate yielded 3-ethoxymethylene-1,5-diphenylpyrrolidine-2,4-dione (2). Reaction of the latter with hydrazine hydrate, secondary amines 7a-c or urea afforded the corresponding 3-substituted aminomethylene-1,5-diphenylpyrrolidene-2,4-diones 3, 8a-c or 9. On the other hand, condensation of 3 with veratraldehyde (5a) yielded 3-[(3,4-dimethoxybenzylidene)hydrazinomethylene]-1,5-diphenylpyrrolidine- 2,4-dione (6). Whereas, cyclization of 9 with the reactive malonate ester 11 produced 3-[(5-butyl-4-hydroxy-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-1-yl) methylene]-1,5-diphenylpyrrolidine-2,4-dione (12). The condensation of some selected aromatic aldehydes 5a-c and addition of morpholine (7c) or piperidine (7d) to some of the resulting 3-arylidene-1,5-diphenylpyrrolidine-2,4-diones 13b, c gave the respective 3-substituted methyl-4-hydroxy-1,5-diphenyl-delta 3-pyrrolin-2-ones 14a-c. Selected members of the new series were screened for their in vitro antimicrobial, anti-HIV-1 and antineoplastic activities. Two compounds 14a, b showed pronounced inhibitory activities against Gram-positive bacteria; whereas, in the in vitro anti-HIV-1 screening, only one compound 13c displayed a moderate activity. However, in the antineoplastic screening protocol, the tested compounds were devoid of activity.
Asunto(s)
Fármacos Anti-VIH/síntesis química , Antiinfecciosos/síntesis química , Antineoplásicos/síntesis química , Pirrolidinonas/síntesis química , Antibacterianos , Fármacos Anti-VIH/farmacología , Antiinfecciosos/farmacología , Antineoplásicos/farmacología , Bacterias/efectos de los fármacos , Fenómenos Químicos , Química Física , Ensayos de Selección de Medicamentos Antitumorales , Hongos/efectos de los fármacos , VIH-1/efectos de los fármacos , Humanos , Indicadores y Reactivos , Espectroscopía de Resonancia Magnética , Pruebas de Sensibilidad Microbiana , Pirrolidinonas/farmacología , Espectrofotometría Infrarroja , Relación Estructura-Actividad , Células Tumorales CultivadasRESUMEN
The synthesis of some 6-substituted 3,5-dioxo- and 3-thioxo-5-oxo-2,3,4,5-tetrahydro-1,2,4-triazines for possible antineoplastic activity is reported. The assigned structures were substantiated by IR, NMR, and mass spectral studies of representative members of the series. Four compounds were tested against P-388 lymphocytic leukemia and were inactive.
Asunto(s)
Antineoplásicos/síntesis química , Triazinas/síntesis química , Animales , Antineoplásicos/uso terapéutico , Leucemia Experimental/tratamiento farmacológico , Métodos , Ratones , Triazinas/farmacología , Triazinas/uso terapéuticoRESUMEN
The synthesis of some derivatives of substituted 7-hydroxy-5H-1.3.4-thiadiazolo[3.2-a]pyrimidin-5-ones, as possible antimicrobial agents, is described. The IR, NMR and MS data of representative members of the series are reported. Proposed common fragmentation pathways for this series are deduced.