RESUMEN
In this study, 21 new compounds having 2-methyl-6-benzylidenethiazolo[3,2-b]-1,2,4-triazol-5(6H)-one (2-4) and 2-methyl-6-(alpha-aminobenzyl)thiazolo[3,2-b]-1,2,4-triazole-5-ol (2a-4g) structures were synthesized. The structures of the compounds were proved by spectral and elemental analysis. All of the compounds synthesized were tested for their anti-inflammatory actively and ulcerogenic potential in mice at 10, 20 and 40 mg/kg dose levels. Compound 4b showed higher anti-inflammatory activity than the analogue derivatives and indometacin (CAS 53-86-1), used as a reference drug, at 10 mg/kg dose level. Generally, the compounds were found to be more reliable than indometacin since they did not cause any reaction in the stomach.
Asunto(s)
Antiinflamatorios no Esteroideos/síntesis química , Antiinflamatorios no Esteroideos/farmacología , Tiazoles/síntesis química , Tiazoles/farmacología , Triazoles/síntesis química , Triazoles/farmacología , Animales , Antiinflamatorios no Esteroideos/toxicidad , Carragenina , Fenómenos Químicos , Química Física , Edema/inducido químicamente , Edema/prevención & control , Femenino , Espectroscopía de Resonancia Magnética , Masculino , Ratones , Espectrofotometría Infrarroja , Úlcera Gástrica/inducido químicamente , Úlcera Gástrica/patologíaRESUMEN
In this study, the synthesis of 3-[1-(4-(2-methylpropyl)phenyl)ethyl]-1,2,4-triazole-5-thione (2) and its condensed derivatives 6-benzylidenethiazolo[3,2-b]-1,2, 4-triazole-5(6H)-ones (2a-u) are described. The structures of the compounds were elucidated by spectral and elemental analysis. In the pharmacological studies, anti-inflammatory activities of these compounds have been screened. Among the compounds examined, the compounds 2 and 2g possessed the most prominent and consistent activity. In gastric ulceration studies the synthesized compounds were generally found to be safe at a 200 mg/kg dose level.
Asunto(s)
Antiinflamatorios no Esteroideos/síntesis química , Triazoles/síntesis química , Animales , Antiinflamatorios no Esteroideos/química , Antiinflamatorios no Esteroideos/farmacología , Evaluación de Medicamentos , Femenino , Masculino , Espectrometría de Masas , Ratones , Estructura Molecular , Triazoles/química , Triazoles/farmacologíaRESUMEN
In this study, the synthesis of some new 2-thioxo-1,2,3,4-tetrahydropyrimidines and their condensed derivatives, thiazolo[3,2-a]pyrimidines, are described. The structures of the compounds were confirmed by 1R, 1H-NMR, 13C-NMR, and mass spectroscopy. The direct high-performance liquid chromatographic separation of the compounds on derivatized cellulose chiral stationary phases such as cellulose tris(3,5-dimethylphenylcarbamate) (OD), cellulose tris(4-methylphenylcarbamate) (OG), and cellulose tris(4-methylbenzoate) (OJ) was studied. All of the compounds were screened for their antiinflammatory activity and also investigated histopathologically. Compounds 3 and 1a were found to be the most promising antiinflammatory agents in this group.
Asunto(s)
Antiinflamatorios no Esteroideos/síntesis química , Pirimidinas/síntesis química , Animales , Antiinflamatorios no Esteroideos/química , Antiinflamatorios no Esteroideos/farmacología , Antiinflamatorios no Esteroideos/toxicidad , Carragenina , Edema/inducido químicamente , Edema/patología , Edema/prevención & control , Femenino , Masculino , Ratones , Pirimidinas/química , Pirimidinas/farmacología , Pirimidinas/toxicidad , EstereoisomerismoRESUMEN
Sixteen new 2-benzylidene-7-methyl-3-oxo-5-(substituted phenyl)-2, 3-dihydro-5H-thiazolo[3,2-a]pyrimidine-6-carboxylic acid methyl esters (1a-4d) have been synthesized by reacting 1,2,3,4-tetrahydropyrimidine-2-thiones (1-4) with chloroacetic acid and appropriate benzaldehydes in a single step. Their structures have been proved by IR, 1H NMR, mass spectra and elemental analysis. The compounds were tested for their anti-inflammatory activities. Test results revealed that compounds 1b, 1c, 4a and 4c exerted moderate anti-inflammatory activity at the 100 mg/kg dose level compared with indomethacin.
Asunto(s)
Antiinflamatorios no Esteroideos/síntesis química , Antiinflamatorios no Esteroideos/farmacología , Pirimidinas/síntesis química , Pirimidinas/farmacología , Animales , Antiinflamatorios no Esteroideos/química , Femenino , Espectroscopía de Resonancia Magnética , Masculino , Espectrometría de Masas , Ratones , Pirimidinas/química , Espectrofotometría InfrarrojaRESUMEN
Thiazolo[3,2-b]-1,2,4-triazole-5(6H)-ones (4-10) were obtained in a one step synthesis by heating 3-aryl-5-mercapto-1,2,4-triazoles (3a-d) with chloroacetic acid and appropriate aromatic aldehyde in acetic acid and acetic anhydride in the presence of anhydrous NaOAc. Michael type addition of cyclic secondary amines (N-methylpiperazine, piperidine) to 4-10 gave 2-phenyl-6-(alpha-aminoarylmethyl)thiazolo[3,2-b]-1,2,4-triazole-5 -ols (4a-10b). The structures of the compounds were confirmed by spectral and elementary analysis. The compounds synthesized in previous and present studies were investigated for their anti-inflammatory activities.
Asunto(s)
Antiinflamatorios no Esteroideos/síntesis química , Tiazoles/síntesis química , Triazoles/síntesis química , Animales , Antiinflamatorios no Esteroideos/farmacología , Antiinflamatorios no Esteroideos/toxicidad , Carragenina , Edema/inducido químicamente , Edema/prevención & control , Femenino , Espectroscopía de Resonancia Magnética , Masculino , Ratones , Úlcera Gástrica/inducido químicamente , Úlcera Gástrica/patología , Tiazoles/farmacología , Tiazoles/toxicidad , Triazoles/farmacología , Triazoles/toxicidadRESUMEN
In this study, thirty six new 2-benzylidene-7-methyl-3-oxo-5- phenyl-2,3-dihydro-5H-thiazolo[3,2-alpha]pyrimidine-6-carboxylic acid methyl esters were synthesized and characterized by spectral, crystallographic, and elemental analysis. The antiinflammatory activity of the compounds was tested by the carrageenan hind paw edema test. It was found that compound 6a having a 2-meth-oxyphenyl group at position 5 and a benzylidene group at position 2 was the most potent compound in this series. All the compounds that were tested for ulcer activity gave positive results.
Asunto(s)
Antiinflamatorios no Esteroideos/síntesis química , Compuestos Heterocíclicos/síntesis química , Pirimidinas/síntesis química , Tiazoles/síntesis química , Animales , Antiinflamatorios no Esteroideos/uso terapéutico , Carragenina , Edema/inducido químicamente , Edema/tratamiento farmacológico , Femenino , Miembro Posterior , Masculino , Ratones , Pirimidinas/uso terapéutico , Úlcera Gástrica/inducido químicamente , Úlcera Gástrica/tratamiento farmacológico , Relación Estructura-Actividad , Tiazoles/uso terapéuticoRESUMEN
The synthesis of a series of thiazolo[3,2-a]pyrimidine derivatives were described. The structures of the compounds were elucidated by IR, 1H-NMR, 13C and elementary analysis. The compounds were evaluated for their calcium antagonistic activities using nifedipine as standard compound. All of the compounds were found to be less potent than nifedipine.
Asunto(s)
Bloqueadores de los Canales de Calcio/síntesis química , Pirimidinas/síntesis química , Tiazoles/síntesis química , Animales , Bloqueadores de los Canales de Calcio/farmacología , Femenino , Cobayas , Íleon/efectos de los fármacos , Íleon/metabolismo , Técnicas In Vitro , Masculino , Nifedipino/farmacología , Pirimidinas/farmacología , Tiazoles/farmacologíaRESUMEN
The synthesis of amide prodrugs of some 2-arylpropionic acids (ibuprofen, naproxen, diclofenac and ketorolac) and the enantiomeric separation of these compounds are reported in this paper. The compounds were prepared from the corresponding 2-arylpropionic acids and (R-(-)-2-amino-1-butanol in the presence of N,N'-dicyclohexylcarbodiimide (DCC). Enantiomers were separated by preparative chromatography or crystallisation. The structure were confirmed by infrared, nuclear magnetic resonance and elementary analysis. The compounds prepared in the study have significant analgesic activity.
Asunto(s)
Amidas/síntesis química , Antiinflamatorios/síntesis química , Profármacos/síntesis química , Propionatos/síntesis química , Administración Tópica , Amidas/efectos adversos , Amidas/farmacocinética , Animales , Antiinflamatorios/efectos adversos , Antiinflamatorios/farmacocinética , Cristalización , Espectroscopía de Resonancia Magnética , Masculino , Ratones , Profármacos/efectos adversos , Profármacos/farmacocinética , Propionatos/efectos adversos , Propionatos/farmacocinética , Absorción Cutánea , Estereoisomerismo , Úlcera Gástrica/inducido químicamenteRESUMEN
Twenty new compounds having 2-methyl-6-benzylidenethiazolo[3,2-b]- 1,2,4-triazole-5(6H)-one (2a-d) and 2-methyl-6-(alpha-aminobenzyl)thiazolo-[3,2-b]-1,2,4- triazole-5-ol (5-20) structures were synthesized. Their structures were confirmed by elemental and spectroscopic analysis and their platelet aggregation inhibitory activities were investigated.