Efficient one-pot, three-component procedure to prepare new α-aminophosphonate and phosphonic acid acyclic nucleosides

Laila Baddi , Driss Ouzebla , Az-Eddine El Mansouri , Michael Smietana , Jean-Jacques Vasseur (1) , Hassan Lazrek

1 IBMM - Institut des Biomolécules Max Mousseron [Pôle Chimie Balard]

An efficient one-pot three-component Kabachnik-Fields reaction of aldehydes (acyclic nucleosides), amines (or amino acid), and triethyl phosphite proceeded for the synthesis of aminophosphonates using natural phosphate coated with iodine (I-2@NP) as a catalyst. The novel alpha-aminophosphonate and phosphonic acid acyclic nucleosides were tested for their anti-HCV and anti-HIV activities. The molecular docking showed that the non-activity of these compounds could be due to the absence of hydrophobic pharmacophores.

Mots clés: DOPED NATURAL PHOSPHATE; SOLVENT-FREE CONDITIONS; AMINO PHOSPHONATES; CARBONYL-COMPOUNDS; FACILE SYNTHESIS; INHIBITORS; DERIVATIVES; IODINE; DESIGN; PROTECTION

Domaines: Chimie analytique; Chimie thérapeutique; Chimie organique; Chimie

Laila Baddi, Driss Ouzebla, Az-Eddine El Mansouri, Michael Smietana, Jean-Jacques Vasseur, et al.. Efficient one-pot, three-component procedure to prepare new α-aminophosphonate and phosphonic acid acyclic nucleosides. Nucleosides, Nucleotides and Nucleic Acids, In press, pp.1-25. ⟨10.1080/15257770.2020.1826516⟩. ⟨hal-02989697⟩