Design, synthesis, and anti-TMV bioactivities of nucleobase phosphonate analogs. (2nd December 2017)

• Record Type: Journal Article
• Authors: Li, Zhen-Xing; Fang, He-Shu; Shao, Wu-Bin; Wang, Pei-Yi; Wu, Zhi-Bing; Yang, Song
• Is Part Of: Phosphorus, sulfur, and silicon and the related elements. Volume 192:Number 12(2017)
• Page Start: 1279
• Page End: 1285
• Publication Date: 2017-12-02
• Subjects: Nucleobase analogs -- phosphonates -- synthesis -- antiviral -- molecular docking; Sulfur compounds -- Periodicals; Organosulfur compounds -- Periodicals; Phosphorus compounds -- Periodicals; Organophosphorus compounds -- Periodicals; Silicon compounds -- Periodicals; Organosilicon compounds -- Periodicals; 546
• DOI: 10.1080/10426507.2017.1321649
• Languages: English
• ISSNs: 1042-6507

Abstract

GRAPHICAL ABSTRACT: ABSTRACT: A series of novel nucleobase derivatives and their analogues possessing diethoxyphosphoryl scaffolds were synthesized through four-step reactions and screened for their antiviral activity toward tobacco mosaic virus (TMV). Preliminary bioassays suggested that some of these simple structures displayed appreciable anti-TMV activity in vivo. Among them, compound (diethoxyphosphoryl)methyl 4-[2-(1H-benzo[d][1, 2, 3]triazol-1-yl)acetamido]-benzoate (a-3 ) exerted the strongest chemotherapeutic and protective effects against TMV with the rates of 52.8 and 72.2% at the dosage of 500 µg/mL, respectively, which were comparable with those of the commercial agricultural antiviral agent ningnanmycin (54.2 and 70.2%). Molecular docking with TMV helicases revealed that compounda-3 had strong interactions with receptor amino acid residues. Given the facile synthetic route and significant chemotherapeutic and protective potentials, compounda-3 could be further studied and exploited as a promising antiviral candidate.