title: Asymmetric Synthesis and Bioselective Activities of α-Amino-phosphonates Based on the Dufulin Motif.
abstract: 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.
authors.affiliation: State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University , Huaxi District, Guiyang 550025, China.|Department of Chemistry, Huaibei Normal University , Anhui, Huaibei 235000, China.
authors.forename: Guoping
authors.initials: G
authors.lastname: Zhang
authors.affiliation: Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, College of Chemistry, Central China Normal University , Wuhan 430079, China.
authors.forename: Gefei
authors.initials: G
authors.lastname: Hao
authors.affiliation: State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University , Huaxi District, Guiyang 550025, China.
authors.forename: Jianke
authors.initials: J
authors.lastname: Pan
authors.affiliation: State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University , Huaxi District, Guiyang 550025, China.
authors.forename: Jian
authors.initials: J
authors.lastname: Zhang
authors.affiliation: State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University , Huaxi District, Guiyang 550025, China.
authors.forename: Deyu
authors.initials: D
authors.lastname: Hu
authors.affiliation: State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University , Huaxi District, Guiyang 550025, China.
authors.forename: Baoan
authors.initials: B
authors.lastname: Song
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D052160:Benzothiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D017799:Cucumovirus / Q000187:drug effects; D062105:Molecular Docking Simulation; D015394:Molecular Structure; D063065:Organophosphonates / Q000737:chemistry; D013237:Stereoisomerism; D014027:Tobacco Mosaic Virus / Q000187:drug effects
chemical_list: D000998:Antiviral Agents; D052160:Benzothiazoles; D063065:Organophosphonates; C576734:dufulin
keywords: asymmetric synthesis; bioselective activity; cucumber mosaic virus coat protein; florescence spectroscopy; molecular docking; α-aminophosphonate