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摘要
The asymmetric synthesis of enantiomerically pure alpha-aminophosphonates with high and bioselective activities is a challenge. Here, we report that both enantiomers of a-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 mu g/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 alpha-aminophosphonate and cucumber mosaic virus coat protein (CMV-CP) via florescence spectroscopy and molecular docking.
