Asymmetric Synthesis and Bioselective Activities of α-Amino-phosphonates Based on the Dufulin Motif.
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.
['Zhang|Guoping|G|', 'Hao|Gefei|G|', 'Pan|Jianke|J|', 'Zhang|Jian|J|', 'Hu|Deyu|D|', 'Song|Baoan|B|']
D000998:Antiviral Agents D052160:Benzothiazoles D017799:Cucumovirus D062105:Molecular Docking Simulation D015394:Molecular Structure D063065:Organophosphonates D013237:Stereoisomerism D014027:Tobacco Mosaic Virus
asymmetric synthesis bioselective activity α-aminophosphonate cucumber mosaic virus coat protein florescence spectroscopy molecular docking