title: D and E rings may not be indispensable for antofine: discovery of phenanthrene and alkylamine chain containing antofine derivatives as novel antiviral agents against tobacco mosaic virus (TMV) based on interaction of antofine and TMV RNA.
abstract: On the basis of the interaction of antofine and tobacco mosaic virus (TMV) RNA, a series of phenanthrene and alkylamine chain containing antofine derivatives 1-41 were designed, synthesized, and systematically evaluated for their antiviral activity against TMV. The results showed that most of these compounds exhibited good to excellent anti-TMV activity, which indicated that the D and E rings of antofine may not be indispensable. Phenanthrene is important for these compounds, but not the more the better. Phenanthrene, benzene rings, and alkylamine chain containing compounds exhibited good antiviral activity. The optimum compounds, 10, 18, and 19, displayed higher activity than precursor antofine and commercial ribavirin, thus emerging as new lead compounds. The novel concise structure provides another new template for antiviral studies.
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: Peng
authors.initials: P
authors.lastname: Wei
authors.forename: Yuxiu
authors.initials: Y
authors.lastname: Liu
authors.forename: Qingmin
authors.initials: Q
authors.lastname: Wang
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D015195:Drug Design; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D015394:Molecular Structure; D010616:Phenanthrenes / Q000737:chemistry / Q000494:pharmacology; D010618:Phenanthrolines / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D012367:RNA, Viral / Q000378:metabolism; D013329:Structure-Activity Relationship; D014027:Tobacco Mosaic Virus / Q000187:drug effects
chemical_list: D000998:Antiviral Agents; D007211:Indoles; D010616:Phenanthrenes; D010618:Phenanthrolines; D012367:RNA, Viral; C473343:antofine; C031181:phenanthrene
keywords: alkylamine chain; antiviral activity; antofine derivatives; phenanthrene; structure−activity relationship; tobacco mosaic virus