Synthesis, NMR, X-ray crystallography and bioactivity of some α-aminophosphonates

Abstract

The synthesis of some new α-aminophosphonates (4a-l) was accomplished by one pot reaction of equimolar quantities of 2-amino-4-chlorophenol (1), various aromatic aldehydes (2a-l) and diethylphosphite (3) in dry toluene at reflux temperature. Products 4a-l were characterized by IR, 1 H, 13 C, 31 P NMR and in the case of 4g by X-ray crystal diffraction data.

Diethyl [(5-chloro-2-hydroxyanilino)(4-chlorophenyl)methyl]phosphonate

“…For applications of -aminophosphonates, see: Allen et al (1989); Baylis et al (1984); Fields (1999); Hirschmann et al (1994); Kafarski & Lejczak (1991); Miliszkiewicz et al (1992). For the antibacterial activity of the title compound, see: Syam Prasad et al (2007). For related structures, see: Boehlow et al (1997); Yang et al (2005); Sawka- Dobrowolska & Kowalik (1985); Sawka-Dobrowolska & Rułko (1987); Sanders et al (1996); Ezra & Collin (1973).…”

“…As a result, a variety of synthetic approaches have been developed for the synthesis of α-aminophosphonates. The title compound (I) exhibits antibacterial activity against Gram positive as well as Gram negative bacteria (Syam et al, 2007) The molecular structure of the title compound is shown in Fig. 1.…”

Synthesis, Computational Studies, Molecular Docking, Anti‐inflammatory and Antioxidant Activities of α‐Aminophosphonates Incorporating an Azo Chromophore for Polyester Printing Application

“…The computed quantum chemical parameters could be able to explain this disparity. Theoretically, compared to the other mono substituted electron donating phosphonates, Compound IIIa has higher electrophilicity index (5.7903 eV) and lower occupied molecular orbital (LUMO) energy (À 2.7538 eV), which could account for why it reacts more quickly as an electrophile and increases its capacity to accept the target protein by increasing activity (Table 3, 4).…”

“…Synthetic α-aminophosphate derivatives have attracted interest due to their distinct biological activity and chemical properties. [1] Aminophosphates are synthesized to provide a variety of molecules with varied therapeutic properties [2][3][4][5][6][7][8][9][10][11][12][13][14][15][16] (see Figure 1). On the other hand, the development of synthetic dyes to suit various industrial demands was encouraged by the growth of textile industries.…”

Synthesis and Characterization of Aminophosphonate Containing Chitosan Polymer Derivatives: Investigations of Cytotoxic Activity and in Silico Study of SARS-CoV-19

“…Phosphorylated chitin (P-chitin) and chitosan (P-chitosan) were prepared by the reaction of chitin or chitosan with orthophosphoric acid and urea in DMF [ 23 ] with phosphorous pentoxide in methane sulphonic acid [ 24 ]. The amino phosphonates are among the most common organophosphorus derivatives and have been used inantiviral, antibacterial, antifungal, and anticancer activities [ 25 , 26 , 27 , 28 , 29 , 30 ]. Many of the Schiff base chitosan derivatives exhibit pharmacological properties likeantimicrobial and anticancer shown in Figure 3 [ 31 , 32 ].…”