Design, synthesis, and anti-TMV bioactivities of nucleobase phosphonate analogs
| Autor: | He-Shu Fang, Song Yang, Wu-Bin Shao, Pei-Yi Wang, Li Zhenxing, Zhi-Bing Wu |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
0301 basic medicine
010405 organic chemistry Stereochemistry Organic Chemistry Base analog 01 natural sciences Biochemistry Phosphonate 0104 chemical sciences Nucleobase Inorganic Chemistry 03 medical and health sciences chemistry.chemical_compound 030104 developmental biology chemistry Design synthesis Tobacco mosaic virus |
| Zdroj: | Phosphorus, Sulfur, and Silicon and the Related Elements. 192:1279-1285 |
| ISSN: | 1563-5325 1042-6507 |
| DOI: | 10.1080/10426507.2017.1321649 |
| Popis: | 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 compound a-3 had strong interactions with receptor amino acid residues. Given the facile synthetic route and significant chemotherapeutic and protective potentials, compound a-3 could be further studied and exploited as a promising antiviral candidate. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|