RESUMEN
A series of 7-(2-substituted phenylthiazolidinyl)-benzopyran-2-one derivatives have been synthesized by reaction of 7-amino-4-methyl-benzopyran-2-one (1) with an appropriate substituted aldehydes to obtain various Schiff bases (3a-k) which on treatment with thioglycolic acid afforded the title compounds (4a-k). Purity of the compounds has been confirmed by TLC. Structure of these compounds were established on the bases IR, 1H NMR, 13C NMR and Mass spectral data. Schiff bases and title compounds were evaluated for antibacterial and antifungal activities against various bacterial and fungal strains. The results showed that compounds 3d, 3f, 4d, 4f and 4i (100 microg/ml) exhibited good antibacterial and antifungal activity as that of standard antibiotics Ciprofloxacin and Griseofulvin.
Asunto(s)
Antiinfecciosos/síntesis química , Antiinfecciosos/farmacología , Cumarinas/síntesis química , Cumarinas/farmacología , Tiazolidinas/química , Antiinfecciosos/química , Bacterias/efectos de los fármacos , Cumarinas/química , Hongos/efectos de los fármacos , Análisis EspectralRESUMEN
A novel series of 14 new isonicotinyl hydrazide derivatives 2a-g, 3a-g containing a 4-thiazolidinone / 2-azetidinone nucleus were synthesized by reacting N'-substituted arylidene / heteroarylidene isonicotinyl hydrazide 1a-g with thioglycollic acid in the presence of dry benzene and with chloroacetyl chloride in the presence of triethylamine, respectively. Structures of all newly synthesized compounds were characterized on the basis of elemental analyses and spectral data (IR and (1)H-NMR). All the title compounds were tested for their in-vitro antimycobacterial activity against Mycobacterium tuberculosis H(37)Rv using Alamar-Blue susceptibility test, and the activity is expressed as the minimum inhibitory concentration (MIC) in microg/mL. Among the series, compounds 2b, 2g, 3b, and 3g displayed an encouraging antimycobacterial activity profile as compared to that of the reference drugs isoniazid / rifampicin.
Asunto(s)
Antibacterianos/síntesis química , Antibacterianos/farmacología , Isoniazida/análogos & derivados , Isoniazida/farmacología , Mycobacterium tuberculosis/efectos de los fármacos , Isoniazida/síntesis química , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Relación Estructura-ActividadRESUMEN
A novel series of coumarinyl Mannich bases (3a-1) have been synthesized by reacting 3-acetyl coumarin (1) with various substituted secondary amines (2a-1) in presence of paraformaldehyde. The structures of the newly synthesized compounds were characterized by IR, 1H NMR, 13C NMR and HRMS (high resolution mass spectral) data. Title compounds were screened for in vivo acute anti-inflammatory activity using the carrageenan-induced rat paw edema assay model. Among the compounds tested, 3-[3-(diethylamino)propanoyl]-2H-chromen-2-one (3a)and 3-[3-(piperidine-1-yl) propanoyl]-2H-chromen-2-one (3c) showed 63.1 and 66.7% inhibition, respectively, as compared to the standard drug diclofenac (CAS 15307-86-5, 68.8%). These potent compounds showed encouraging analgesic andantipyretic activities.
Asunto(s)
Analgésicos no Narcóticos/síntesis química , Analgésicos no Narcóticos/farmacología , Antiinflamatorios/síntesis química , Antiinflamatorios/farmacología , Cumarinas/síntesis química , Cumarinas/farmacología , Bases de Mannich/síntesis química , Bases de Mannich/farmacología , Ácido Acético , Analgésicos no Narcóticos/toxicidad , Animales , Antiinflamatorios/toxicidad , Cumarinas/toxicidad , Evaluación Preclínica de Medicamentos , Femenino , Fiebre/inducido químicamente , Fiebre/tratamiento farmacológico , Indicadores y Reactivos , Espectroscopía de Resonancia Magnética , Masculino , Bases de Mannich/toxicidad , Espectrometría de Masas , Ratones , Dimensión del Dolor/efectos de los fármacos , Solventes , Espectrofotometría Infrarroja , Espectrofotometría Ultravioleta , Espectroscopía Infrarroja por Transformada de Fourier , Úlcera Gástrica/inducido químicamente , Úlcera Gástrica/patologíaRESUMEN
A novel series of coumarinyl amides (IVa-l) have been synthesized by reacting 7-amino-4-methylcoumarin (III) with various substituted aromatic acid chlorides. IR, 1H NMR, 13C NMR and HRMS spectral data characterized the structure of the synthesized compounds. The title compounds were screened for in vivo acute anti-inflammatory activity using the carrageenan-induced rat paw edema assay model. Among the compounds tested, 2-chloro-N-(4-methyl-2-oxo-2H-chromen-7-yl)benzamide (IVb) and 4-chloro-N-(4-methyl-2-oxo-2H-chromen-7-yl)benzamide (IVc) showed 60.5 and 62.3% edema protection, respectively, as compared to the standard drug diclofenac (CAS 15307-86-5) (63.5%) after third hour. Compounds N-(4-methyl-2-oxo-2H-chromen-7-yl)-4-nitrobenzamide (IVf) and N-(4-methyl-2-oxo-2H-chromen-7-yl)cinnamamide (IVg) showed moderate activity. The new compounds have been also tested for in vivo analgesic activity. Quantitative structure-activity relationship studies indicated that the chloro substitution at the aromatic ring enhanced the anti-inflammatory activity (IVb and IVc). These compounds were also found to provide significant protection in acetic acid induced writhing animal model, showing remarkable analgesic activity. Compounds IVb and IVc showed 55.1% and 56.3% protection, respectively, as compared to acetylsalicylic acid (CAS 50-78-2) (57.7%).