Asymmetric Synthesis and Bioselective Activities of α-Amino-phosphonates Based on the Dufulin Motif

详细信息    查看全文

• 作者：Guoping Zhang ; Gefei Hao ; Jianke Pan ; Jian Zhang ; Deyu Hu ; Baoan Song
• 刊名：Journal of Agricultural and Food Chemistry
• 出版年：2016
• 出版时间：June 1, 2016
• 年：2016
• 卷：64
• 期：21
• 页码：4207-4213
• 全文大小：376K
• 年卷期：0
• ISSN：1520-5118

文摘

The asymmetric synthesis of enantiomerically pure α-aminophosphonates with high and bioselective activities is a challenge. Here, we report that both enantiomers of α-aminophosphonates bearing the N-benzothiazole moiety can be prepared in high yields (up to 99%) and excellent enantioselectivities (up to 99% ee) by using chiral thiourea organocatalysts. Evaluation of the antiviral activities of our reaction products against cucumber mosaic virus (CMV) led to promising hits with high and selective biological activities, wherein (R)-enantiomers exhibit higher biological activities than the corresponding (S)-enantiomers. Especially, compound (R)-3b with excellent anti-CMV activity (curative activity, 72.3%; protection activity, 56.9%; and inactivation activity, 96.9%) at 500 μg/mL emerged as a potential inhibitor of the plant virus. The difference in the selective bioactivity could be affected by the combination mode of the three-dimensional space between the enantiomers of α-aminophosphonate and cucumber mosaic virus coat protein (CMV-CP) via florescence spectroscopy and molecular docking.