Synthesis and antiviral activities of cyanoacrylate derivatives containing an alpha-aminophosphonate moiety.
Target compounds 8 were obtained by the reaction of alkyl 2-cyano-3,3-dimethylthioacrylate or cyarylamide (7a-7e) and alpha-aminobenzylphosphonate (5a-5e) under reflux condition using ethanol as solvent. Their structures were clearly verified by spectroscopic data (IR and 1H, 13C, and 31P NMR) and elemental analysis. These compounds were shown to be antivirally active in the bioassay. It was found that title compounds 8d and 8e had the same inactivation effect against tobacco mosaic virus (EC 50 = 55.5 and 55.3 microg/mL) as the commercial product ningnanmycin (EC 50 = 50.9 microg/mL). To the best of our knowledge, this is the first report on the synthesis and antiviral activity of cyanoacrylate derivatives containing an alpha-aminophosphonate moiety.
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.
Ning
N
Long
Xue-Jian
XJ
Cai
Bao-An
BA
Song
Song
S
Yang
Zhuo
Z
Chen
Pinaki S
PS
Bhadury
De-Yu
DY
Hu
Lin-Hong
LH
Jin
Wei
W
Xue
D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D001681:Biological Assay; D003487:Cyanoacrylates / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D015394:Molecular Structure; D010935:Plant Diseases / Q000821:virology; D013329:Structure-Activity Relationship; D014026:Nicotiana / Q000821:virology; D014027:Tobacco Mosaic Virus / Q000187:drug effects*
D000998:Antiviral Agents; D003487:Cyanoacrylates