Antiviral stereoisomers of 3,5-bis(2-hydroxybut-3-en-1-yl)-1,2, 4-thiadiazole from the roots of Isatis indigotica
Ming-Hua Chen, Sheng Lin, Ya-Nan Wang, Cheng-Gen Zhu, Yu-Huan Li, Jian-Dong Jiang, Jian-Gong Shi
Chinese Chemical Letters
Four stereoisomers of 3,5-bis(2-hydroxybut-3-en-1-yl)-1,2,4-thiadiazole, named insatindigothiadiazoles A–D (1a–1d), were isolated from the roots of Isatis indigotica. Their structures were determined by spectroscopic analysis; specifically, the absolute configurations were assigned by using the MPA determination rule based on ΔδRS values of MPA esters, and supported by electronic CD (ECD) calculations. Proposed biosynthetic pathways and preliminary investigations of the biological activities of 1a–1dagainst influenza virus A (H3N2), Coxsackie virus B3, and/or HSV-1 are also discussed.
Circular dichroism, Absolute configuration, Medicinal