Synthesis and Antiviral Bioactivities of 2-Cyano-3-substituted-amino(phenyl) Methylphosphonylacrylates (Acrylamides) Containing Alkoxyethyl Moieties

Abstract

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.

Metal and carbene organocatalytic relay activation of alkynes for stereoselective reactions

“…TMV is known to infect more than 400 plant species such as tobacco, tomato, potato and cucumber to cause tremendous economic loss worldwide 45,46 . Built on our previous studies in this area to treat plant virus diseases 47,48 , our preliminary studies here found that the isatin-derived alkene compound 5k showed a promising 42.6% inhibition rate against TMV infection. The positive control experiment using the commercially used drug Ningnanmycin 45,49 showed 56.2% inhibition rate (Fig.…”

Design, synthesis, antiviral activity and mode of action of phenanthrene-containingN-heterocyclic compounds inspired by the phenanthroindolizidine alkaloid antofine

“…In recent decades, many efforts have been made to develop novel, potent and structurally concise antiviral agents. A series of chemicals have been found to possess antiviral activity, such as pyrazole derivatives, cyanoacrylate derivatives, α ‐aminophosphonate derivatives, N ‐(pyrimidin‐5‐yl)‐ N ′‐phenylureas and some natural products . However, there are only a few reports on economically viable antiviral chemicals available for application in agriculture, so there is still great scope for further research in this field.…”

First Discovery and Stucture-Activity Relationship Study of Phenanthroquinolizidines as Novel Antiviral Agents against Tobacco Mosaic Virus (TMV)

“…Because of the unsatisfactory cure rate (30-60%) of common antiviral agents (Ningnanmycin, Ribavirin, Virus A, et al) and economic loss of tobacco, many efforts have been done to develop novel, potent and structure concise antiviral agents. Some chemicals, such as triazolyl compounds [3], pyrazole derivatives [4,5], cyanoacrylate derivatives [5,6], a-aminophosphonate derivatives [5,7], N-(pyrimidin-5-yl)-N9-phenylureas [8], and some natural products [9][10][11], have been found to possess antiviral activity. However, there are only a few reports on economically viable antiviral chemicals available for application in agriculture [12], so there still lies a great deal of scope for further research in this field.…”