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Synthesis and Antiviral Activity of Novel 1,3,4-Thiadiazine Derivatives

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A series of novel 1,3,4-thiadiazine derivatives were synthesized via chemical optimization on phthiobuzone. Their anti-herpes simplex virus (HSV) activities in vitro were also tested. Several compounds exhibited more highly potent anti-HSV activity and much higher selectivity index (SI) values than those of phthiobuzone. The most potent anti-HSV compound was 4f, which showed marked inhibition against HSV-1 (IC(50)=77.04 µg/ml) and HSV-2 (IC(50)=30.00 µg/ml). Meanwhile it had low cytotoxicity (CC(50)=1000.00 µg/ml), resulting in high (SI(HSV-1)=12.98, SI(HSV-2)=33.33, respectively). Furthermore, a computational study for prediction of absorption, distribution, metabolism, excretion (ADME) properties of compound 4f was performed by determination of topological polar surface area, absorption and Lipinski parameters.

The article is published online in Chemical & Pharmaceutical Bulletin and is free to access.