RESUMEN
Four novel series of 1H-benzotriazole derivatives; containing thiazolin, thiazolidin, thiadiazole and oxadiazole moieties; namely 1-[(3,4-disubstituted thiazolin-2-ylidene)hydrazinocarbonyl]methyl-1H-benzotriazoles 3a-1; 1-[3-substituted 5-ethoxycarbonyl-4-methyl thiazolin-2-ylidene)hydrazinocarbonyl]methyl-1H-benzotriazoles 4a-c; 1-[(3-substituted-4-oxothiazolidin-2-ylidene)hydrazinocarbonyl]methyl-1H- benzotriazoles 5a-d; 1-[(5-substituted aminothiadiazol-2-yl)methyl]-1H-benzotriazoles 6a-c have been synthesized by cyclization of the key intermediates 1-[(substituted thiocarbamoylhydrazinocarbonyl)methyl]-1H-benzotriazoles 2a-d. Furthermore 1-[(5-substituted aminooxadiazol-2-yl)methyl]-1H-benzotriazoles 7a, b were obtained by one-pot synthesis starting from 1H-benzotriazol-1-acetic acid hydrazide. The antiinflammatory activity of representative compounds was evaluated in vivo against indomethacin as a standard using the sponge implantation model of inflammation in rats. Both non-immunological parameters such as exudate volume, total leucocyte count (TLC), and differential leucocyte count (DLC), and immunological parameters, for example neutrophil phagocytic function by reduced cytochrome C levels, and the assay of interleukin-1 beta (IL-1 beta) levels in drug-pre-treated rats, were determined. The ulcerogenic activity of compounds showing marked antiinflammatory activity was also studied. Compounds 3e, 5b and 5c showed antiinflammatory activity comparable to indomethacin, and they also demonstrated minimum ulcerogenic activity.
Asunto(s)
Antiinflamatorios no Esteroideos/síntesis química , Úlcera Gástrica/inducido químicamente , Animales , Antiinflamatorios no Esteroideos/farmacología , Antiinflamatorios no Esteroideos/toxicidad , Benzodiazepinas/síntesis química , Benzodiazepinas/farmacología , Exudados y Transudados/efectos de los fármacos , Exudados y Transudados/metabolismo , Mucosa Gástrica/patología , Interleucina-1/metabolismo , Recuento de Leucocitos , Espectroscopía de Resonancia Magnética , Masculino , Neutrófilos/efectos de los fármacos , Ratas , Espectrofotometría Infrarroja , Úlcera Gástrica/patologíaRESUMEN
Two novel series of triazolothiadiazole derivatives were synthesized, namely: 6-substituted-3-(4-substituted phenoxymethyl)-1,2,4-triazolo[3,4- b] [1,3,4]thiadiazoles and 6-mercapto-3-(4-substituted phenoxy-methyl)-1,2,4-triazolo[3,4- b] [1,3,4]thiadiazoles. The anthelmintic activity of representative compounds was studied.
Asunto(s)
Antihelmínticos/síntesis química , Tiadiazoles/síntesis química , Triazoles/síntesis química , Animales , Antihelmínticos/farmacología , Antihelmínticos/uso terapéutico , Fenómenos Químicos , Química , Parasitosis Intestinales/tratamiento farmacológico , Espectroscopía de Resonancia Magnética , Ratones , Tiadiazoles/farmacología , Tiadiazoles/uso terapéutico , Triazoles/farmacología , Triazoles/uso terapéuticoRESUMEN
Three novel series of benzoquinone derivatives were synthesized, namely: N-(3-aryl-4-phenylthiazolin-2-ylidene)-N-(1,4-benzoquinone carbonyl) hydrazines; N-(3-aryl-5-carbethoxy-4-methylthiazolin-2-ylidene)-N-(1,4- benzoquinone carbonyl)hydrazine and N-(3-arylthiazolin-4-one-2-ylidene)-N-(1,4- benzoquinone carbonyl) hydrazines. These series were prepared by oxidation of the new hydroquinone precursors. The antimicrobial activity of representative compounds of benzoquinone, as well as of hydroquinone derivatives was studied.
Asunto(s)
Antiinfecciosos/síntesis química , Benzoquinonas , Quinonas/síntesis química , Tiazoles/síntesis química , Antibacterianos , Candida albicans/efectos de los fármacos , Fenómenos Químicos , Química , Escherichia coli/efectos de los fármacos , Espectroscopía de Resonancia Magnética , Pruebas de Sensibilidad Microbiana , Staphylococcus aureus/efectos de los fármacosRESUMEN
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 several novel thiosemicarbazone derivatives of steroids, including estrogens and androgens, is described. Evaluation of the products in P 388 Lymphocytic Leukemia indicated no anticancer activity. The endocrinological screening showed that estrogenicity is slightly reduced but not abolished in the thiosemicarbazones derived from estrone-3-methyl ether (compounds 1, 2 and 4). The androgenic activity of the thiosemicarbazones derived from testosterone (compounds 7--9) was more pronounced than that of testosterone. Among the same thiosemicarbazone derivatives 7--9, only o-tolyl derivative 8 exhibited anabolic activity.
Asunto(s)
Esteroides/síntesis química , Tiosemicarbazonas/síntesis química , Animales , Antineoplásicos , Estradiol/farmacología , Femenino , Masculino , Ratones , Músculos/efectos de los fármacos , Tamaño de los Órganos/efectos de los fármacos , Próstata/efectos de los fármacos , Ratas , Esteroides/farmacología , Testosterona/farmacología , Tiosemicarbazonas/farmacología , Útero/efectos de los fármacosRESUMEN
New compounds derived from cinchoninic acid esters and amides were prepared. The esters are those derived from p-hydroxy-N-methyldichloroacetanilide (diloxanide) whereas the amides are from piperazine whose hydrogen is substituted by a dichloroacetyl group. The dichloroacetamido group is responsible for the amebicidal activity in several related compounds.