Synthesis and antiviral activities of amide derivatives containing the alpha-aminophosphonate moiety.
Starting from (substituted-)benzaldehydes, the title compounds 6 were synthesized through five step reactions. Benzaldehydes were treated with ammonium hydroxide, followed by dialkyl phosphite, to give dialkyl N-(arylmethylene)-1-amino-1-aryl methylphosphonates ( 3). Phosphonates 3 were then easily hydrolyzed to give dialkyl 1-amino-1-aryl-methylphosphonates 5. Target compounds 6 were then obtained by the reaction of 5 and substituted benzoic or cinnamic acid. Their structures were clearly verified by spectroscopic data (IR, 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 6g, 6l, and 6n had the same inactivation effect of TMV (EC 50 = 54.8, 60.0, and 65.2 microg/mL, respectively) as commercial product Ningnanmycin (EC50 = 55.6 microg/mL). To the best of our knowledge, this is the first report on the synthesis and antiviral activity of amide derivatives containing an alpha-aminophosphonate moiety.
Hu
De-Yu
DY
Center for Research and Development of Fine Chemicals, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, PR China.
Wan
Qiong-Qiong
QQ
Yang
Song
S
Song
Bao-An
BA
Bhadury
Pinaki S
PS
Jin
Lin-Hong
LH
Yan
Kai
K
Liu
Fang
F
Chen
Zhuo
Z
Xue
Wei
W
D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000998:Antiviral Agents / Q000737:chemistry / Q000494:pharmacology*; D019817:Benzoic Acid / Q000737:chemistry; D002934:Cinnamates / Q000737:chemistry; D003562:Cytidine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D063065:Organophosphonates / Q000737:chemistry*; D014027:Tobacco Mosaic Virus / Q000187:drug effects
D000577:Amides; D000998:Antiviral Agents; D002934:Cinnamates; D063065:Organophosphonates; C000594254:ningnanmycin; C029010:cinnamic acid; D003562:Cytidine; D019817:Benzoic Acid