Synthesis and antiviral bioactivities of alpha-aminophosphonates containing alkoxyethyl moieties.

A simple, efficient, and general method has been developed for the synthesis of various alpha-aminophosphonate derivatives 4a-4l by treatment of substituted benzaldehydes and aniline with bis(2-methoxyethyl)- or bis(2-ethoxyethyl) phosphite under microwave irradiation without solvents and catalysts. The products were characterized by elemental analysis, IR, 1H-NMR, 13C- and 31P-NMR spectra. The X-ray crystallographic data of the representative compound 4l was determined. The new alpha-aminophosphonate derivatives were found to possess moderate to good antiviral activity.

[1]  B. Song,et al.  Synthesis, X-ray crystallographic analysis, and antitumor activity of N-(benzothiazole-2-yl)-1-(fluorophenyl)-O,O-dialkyl-α-aminophosphonates , 2006 .

[2]  B. Song,et al.  Synthesis and biological activities of novel dialkyl (4-trifluoromethylphenylamino)-(4-trifluoromethyl or 3-fluorophenyl) methylphosphonates , 2006 .

[3]  A. Holý,et al.  Cytotoxicity of pivoxil esters of antiviral acyclic nucleoside phosphonates: adefovir dipivoxil versus adefovir. , 2005, Biomedical papers of the Medical Faculty of the University Palacky, Olomouc, Czechoslovakia.

[4]  L. Kudryavtseva,et al.  Antimicrobial activity of O,O-diethyl N-alkylaminomethyl-phosphonates and O-ethyl N-alkylaminomethylphosphonic acids , 1986, Pharmaceutical Chemistry Journal.

[5]  D. Hu,et al.  Synthesis and Bioactivity of a-Aminophosphonates Containing Fluorine , 2003, Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry.

[6]  H. R. Hudson,et al.  Aminophosphonic and aminophosphinic acids : chemistry and biological activity , 2000 .

[7]  H. Faiger,et al.  Towards the development of novel antibiotics: synthesis and evaluation of a mechanism-based inhibitor of Kdo8P synthase. , 1999, Bioorganic & medicinal chemistry.

[8]  George M. Sheldrick,et al.  SADABS, Program for Empirical Absorption Correction of Area Detector Data , 1996 .

[9]  Ian Lynch,et al.  Software Reference Manual , 1987 .

[10]  D. A. Shirley Preparation of organic intermediates , 1951 .