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Journal of the Chilean Chemical Society

versão On-line ISSN 0717-9707

Resumo

AZIZ-UR-REHMAN et al. SYNTHESIS, SPECTRAL ANALYSIS AND ANTIBACTERIAL EVALUATION OF 5-SUBSTITUTED-1,3,4-OXADIAZOL-2-YL 4-(4-METHYLPIPERIDIN-1-YLSULFONYL)BENZYL SULFIDES. J. Chil. Chem. Soc. [online]. 2017, vol.62, n.1, pp.3370-3375. ISSN 0717-9707.  http://dx.doi.org/10.4067/S0717-97072017000100013.

Owing to valuable biological activities of 1,3,4-oxadiazole, sulfamoyl and piperidine functionalities, some new 1-(4-{[(5-substituted-1,3,4-oxadiazol-2-yl) thio]methyl}benzene sulfonyl)-4-methylpiperidine (6a-o) derivatives have been introduced. The target molecules were synthesized from different aralkyl/aryl carboxylic acids, 1a-o, through a series of steps. First the compounds, 1a-o, were converted to heterocyclic 1,3,4-oxadiazole nucleophiles, 4a-o. Second an electrophile as 1-(4-bromomethylbenzenesulfonyl)-4-methylpiperidine (5) was synthesized from 4-methylpiperidine. Finally the target compounds, 6a-o, were prepared by reacting 4a-o with 5 in DMF and LiH. The final compounds were structurally elucidated by spectral data of IR, 1H-NMR and EI-MS. All the compounds were screened for their antibacterial evaluation and found to exhibit valuable results.

Palavras-chave : 1,3,4-oxadiazole; 4-methylpiperidine; antibacterial activity; sulfonamide; 1H-NMR; EI-MS.

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