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Chalcones and 1,5-benzothiazepines derived from 4-isobutyl acetophenone having a variety of pharmacophores could be successfully synthesized in good yield, purified, and characterized by spectral studies. These compounds were evaluated for antimicrobial and cytotoxic activities. It was observed from the results that the chalcones possessed better antibacterial activity while the benzothiazepines possessed better antifungal activity. In each case, the contribution of electron-withdrawing groups is remarkable in enhancing the antibacterial or antifungal activity The cytotoxic activity as evidenced by IC50 values is more in the case of benzothiazepines and the results are very encouraging calling for further studies on a number of other cell lines that will enable the usefulness of these compounds. All the computational studies, more or less were consistent with the actual results. The observed - log MIC values from the actual results and the predicted - log MIC values through the PLS method were well correlated supporting the usefulness of these computational studies.
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