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4739970 
Journal Article 
Design, Synthesis, and Antitobacco Mosaic Virus Activity of Water-Soluble Chiral Quaternary Ammonium Salts of Phenanthroindolizidines Alkaloids 
Han, G; Chen, L; Wang, Q; Wu, M; Liu, Y; Wang, Q 
2018 
Yes 
Journal of Agricultural and Food Chemistry
ISSN: 0021-8561
EISSN: 1520-5118 
American Chemical Society 
66 
4 
780-788 
English 
29355318 
WOS:000424313300005 
To study the influence of the substituent at the N-10 position on antiviral activity, the chiral quaternary ammonium salt derivatives of R- and S-tylophorine were designed, synthesized, and evaluated for antiviral activity against tobacco mosaic virus (TMV). The bioassay results indicated that most of the designed structural analogues showed good in vivo anti-TMV activity, among which propargyl quaternary ammonium salt compound S-7b showed the best anti-TMV activities (80.5%, 77.6%, 76.6%, 82.1%) at 500 μg/mL both in vitro and in vivo in the laboratory. In the field trials of antiviral efficacy against TMV, S-7b as well exhibited better activities than control plant virus inhibitors. The stability of compound S-7b was obviously increased, and its solubility was more than 500-times higher than that of S-tylophorine. Therefore, chiral quaternary ammonium salt S-7b was expected to be developed as a promising candidate as an inhibitor of plant virus. 
anti-TMV; derivatives; phenanthroindolizidines alkaloids; quaternary ammonium salts; solubility; stability; structure-activity relationship