title: Design, synthesis, anti-tobacco mosaic virus (TMV) activity, and SARs of 7-methoxycryptopleurine derivatives.
abstract: A series of 7-methoxycryptopleurine derivatives 2-23 were prepared and evaluated for their antiviral activity against tobacco mosaic virus (TMV) for the first time. The bioassay results showed that most of these compounds exhibited excellent in vivo anti-TMV activity, of which 7-methoxycryptopleurine salt derivatives 16, 19, and 23 displayed significantly higher activity than 7-methoxycryptopleurine (1) and commercial ribavirin and ningnanmycin. Salification, the most commonly employed method for modifying physical-chemical properties, did significantly increase antiviral activity, and different salt forms displayed different antiviral effect. This study provides fundamental support for development and optimization of phenanthroquinolizidine alkaloids as potential inhibitors of plant virus.
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering(Tianjin), Nankai University, Tianjin, 300071, China.
authors.forename: Ziwen
authors.initials: Z
authors.lastname: Wang
authors.forename: Anzheng
authors.initials: A
authors.lastname: Feng
authors.forename: Mingbo
authors.initials: M
authors.lastname: Cui
authors.forename: Yuxiu
authors.initials: Y
authors.lastname: Liu
authors.forename: Lizhong
authors.initials: L
authors.lastname: Wang
authors.forename: Qingmin
authors.initials: Q
authors.lastname: Wang
mesh_terms: D000470:Alkaloids / Q000737:chemistry; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D060326:Chemistry Techniques, Synthetic; D015195:Drug Design; D004353:Drug Evaluation, Preclinical / Q000379:methods; D010618:Phenanthrolines / Q000737:chemistry; D011807:Quinolizines / Q000737:chemistry* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D014026:Nicotiana / Q000187:drug effects / Q000821:virology; D014027:Tobacco Mosaic Virus / Q000187:drug effects*
chemical_list: C518787:7-methoxycryptopleurine; D000470:Alkaloids; D000998:Antiviral Agents; D010618:Phenanthrolines; D011807:Quinolizines; C521641:phenanthroquinolizidine
keywords: 7-methoxycryptopleurine; antiviral activity; phenanthroquinolizidine alkaloids; salification; structure-activity relationships; tobacco mosaic virus