Synthesis and antiviral bioactivities of 2-cyano-3-substituted-amino(phenyl) methylphosphonylacrylates (acrylamides) containing alkoxyethyl moieties.
An efficient reaction under microwave irradiation has been developed for the synthesis of a series of novel 2-cyano-3-substituted-amino(phenyl) methylphosphonylacrylates (acrylamides) II. The products obtained in shorter reaction time with moderate yields are fully characterized by elemental analysis, IR, (1)H, (13)C, and (31)P NMR spectral data. The role of introducing various substituents and the effect of incorporating alpha-aminophosphonates with an alkoxyethyl moiety into the parent cyanoacrylate (acrylamide) structure are investigated. Among the studied compounds, both II-17 and II-24 displayed good in vivo curative, protection, and inactivation effects, which were comparable to those of the commercial reference ningnanmycin (inhibitory rates of 58.8, 60.2, 78.9% and 60.0, 58.9, 85.5%, respectively, at 500 mg/L against TMV). To the best of the authors' knowledge, this is the first report on the synthesis and antiviral activity of the title compounds II.
Yang
Jia-Qiang
JQ
Center for Research and Development of Fine Chemicals, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, People's Republic of China.
Song
Bao-An
BA
Bhadury
Pinaki S
PS
Chen
Zhuo
Z
Yang
Song
S
Cai
Xue-Jian
XJ
Hu
De-Yu
DY
Xue
Wei
W
D000178:Acrylamides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D013055:Spectrophotometry, Infrared; D014027:Tobacco Mosaic Virus / Q000187:drug effects
D000178:Acrylamides; D000998:Antiviral Agents