| Summary: | Dipolar cycloaddition of the N-substituted <i>C</i>-(diethoxyphosphonyl)nitrones with <i>N</i><sup>3</sup>-allyl-<i>N</i><sup>1</sup>-benzylquinazoline-2,4-diones produced mixtures of diastereoisomeric 3-(diethoxyphosphonyl)isoxazolidines with a <i>N</i><sup>1</sup>-benzylquinazoline-2,4-dione unit at C5. The obtained compounds were assessed for antiviral and antibacterial activities. Several compounds showed moderate inhibitory activities against VZV with EC<sub>50</sub> values in the range of 12.63–58.48 µM. A mixture of isoxazolidines <i>cis</i>-<b>20c</b>/<i>trans</i>-<b>20c</b> (6:94) was found to be the most active against <i>B. cereus</i> PCM 1948, showing an MIC value 0.625 mg/mL, and also was not mutagenic up to this concentration.
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