Author:

Keywords:

Science & Technology, Life Sciences & Biomedicine, Physical Sciences, Biochemistry & Molecular Biology, Chemistry, Multidisciplinary, Chemistry, isoxazolidines, quinazoline-2, 4-diones, phosphonates, antiviral activity, antimicrobial activity, DERIVATIVES, INHIBITORS, ISOXAZOLIDINE, OPTIMIZATION, DISCOVERY, ANALOGS, POTENT, SERIES, VIRUS, ACIDS, quinazoline-2,4-diones, Anti-Bacterial Agents, Antiviral Agents, Herpes Zoster, Herpesvirus 3, Human, Humans, Organophosphonates, Quinazolines, 0304 Medicinal and Biomolecular Chemistry, 0305 Organic Chemistry, 0307 Theoretical and Computational Chemistry, Organic Chemistry, 3404 Medicinal and biomolecular chemistry, 3405 Organic chemistry

Abstract:

Dipolar cycloaddition of the N-substituted C-(diethoxyphosphonyl)nitrones with N3-allyl-N1-benzylquinazoline-2,4-diones produced mixtures of diastereoisomeric 3-(diethoxyphosphonyl)isoxazolidines with a N1-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 EC50 values in the range of 12.63-58.48 µM. A mixture of isoxazolidines cis-20c/trans-20c (6:94) was found to be the most active against B. cereus PCM 1948, showing an MIC value 0.625 mg/mL, and also was not mutagenic up to this concentration.