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 syntheses of 3-bromo-, 3-substituted aminomethyl-, and 3-(4-substituted sulfamylphenylazo)-4-hydroxy-1,5-diphenyl-pyrrolin-2-ones 4,6 and 8 from 1,5-diphenylpyrrolidine-2,4-dione 3 via bromination aminomethylation and diazocoupling, respectively, are described. The preparation of some 1,5-diphenyl-4-(substituted thiosemicarbazono) pyrrolidin-2-ones 10 and their conversion either to 1,5-diphenyl-4-(substituted thiazol-2-ylhydrazono)pyrrolidin-2-ones 12 or to 1,5-diphenyl-4-(3,4-disubstituted-4-thiazolin-2-ylidenehydrazon o)pyrrolidin-2- ones 13, is also reported. Nine compounds were screened against P-388 lymphocytic leukemia in mice but were inactive. Two compounds (6a and 6b) exhibited in vitro activities against some Gram-positive bacteria.
Asunto(s)
Antiinfecciosos/síntesis química , Antineoplásicos/síntesis química , Hidrazonas/síntesis química , Pirrolidinas/síntesis química , Animales , Antibacterianos , Antiinfecciosos/farmacología , Antineoplásicos/farmacología , Bacterias/efectos de los fármacos , Candida/efectos de los fármacos , Hidrazonas/farmacología , Leucemia P388/tratamiento farmacológico , Ratones , Pruebas de Sensibilidad Microbiana , Pirrolidinas/farmacologíaRESUMEN
Several new 1,3,4-thiadiazole, imidazo[2,1-b]1,3,4-thiadiazole and thiadiazole[3,2-al]pyrimidine derivatives of benzimidazole were synthesized. The compounds were obtained from 1-ethyl or benzyl 2-(2-amino-1,3,4-thiadiazol-5-yl)thiomethylbenzimidazole. The antimicrobial activity of the prepared compounds was studied.
Asunto(s)
Antiinfecciosos/síntesis química , Bencimidazoles/síntesis química , Imidazoles/síntesis química , Pirimidinas/síntesis química , Tiadiazoles/síntesis química , Antibacterianos , Antiinfecciosos/farmacología , Bacterias/efectos de los fármacos , Bencimidazoles/farmacología , Candida albicans/efectos de los fármacos , Imidazoles/farmacología , Espectroscopía de Resonancia Magnética , Espectrometría de Masas , Pruebas de Sensibilidad Microbiana , Pirimidinas/farmacología , Espectrofotometría Infrarroja , Tiadiazoles/farmacologíaRESUMEN
Different new esters of 5-aryl-1,3,4-thiadiazol-2-ylcarbazic acid and dithiocarbazic acid were prepared. In addition, the synthesis of 2-(N,N'-dialkylcarboxy)hydrazino-5-aryl-1,3,4-thiadiazoles is described. IR and NMR data of the new compounds are discussed. Some of these compounds showed a reasonable activity against Gram positive bacteria and fungi.
Asunto(s)
Antiinfecciosos/síntesis química , Tiadiazoles/síntesis química , Antibacterianos , Bacterias/efectos de los fármacos , Fenómenos Químicos , Química , Hongos/efectos de los fármacos , Espectroscopía de Resonancia Magnética , Pruebas de Sensibilidad Microbiana , Espectrofotometría Infrarroja , Tiadiazoles/farmacologíaRESUMEN
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 new 4-[2-alkyl (aryl or aralkyl) amino-1,3,4-thiadiazol-5-yl]-2-substituted quinolines is described. IR, UV, NMR and MS data of representative examples are discussed. Most of the compounds prepared showed a reasonable antifungal and antimicrobial activity.
Asunto(s)
Antiinfecciosos/síntesis química , Antifúngicos/síntesis química , Quinolinas/síntesis química , Antibacterianos , Bacterias/efectos de los fármacos , Hongos/efectos de los fármacos , Quinolinas/farmacologíaRESUMEN
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.
Asunto(s)
Antiinfecciosos/síntesis química , Pirimidinas/síntesis química , Antiinfecciosos/farmacología , Fenómenos Químicos , Química , Pirimidinas/farmacologíaAsunto(s)
Bencimidazoles/síntesis química , Antagonistas de los Receptores Histamínicos H1/síntesis química , Animales , Bencimidazoles/farmacología , Cobayas , Antagonistas de los Receptores Histamínicos H1/farmacología , Íleon/efectos de los fármacos , Peso Molecular , Contracción Muscular/efectos de los fármacos , Músculo Liso/efectos de los fármacosRESUMEN
The use of different alkyl halides as effective cyclodesulfurizing agents was thoroughly studied. N-phenyl-,N'-[o-aminophenyl]-thiourea when treated with different alkyl halides gave rise to 2-phenyl-aminobenzimidazole. The optimum conditions for such cyclodesulfurization reaction were established by using eight equivalents of the alkyl halide, ethyl alcohol as solvent, and 8 h reflux. The reaction was also successfully applied to N-o-tolyl (benzyl or n-butyl)-N'-[o-aminophenyli1-thioureas to give rise to the corresponding 2-substituted aminobenzimidazoles.