Synthesis and Antibacterial Activity of Novel Phosphonate Derivatives Containing Flavonoids

Abstract

By introducing flavonoids group into H-phosphonate, fourteen novel phosphonate derivatives containing flavonoid unit were designed and synthesized. Their structures were characterized by 1 H NMR, 13 C NMR, 31 P NMR, MS, IR and HRMS, and their antibacterial activities were evaluated via turbidimeter test in vitro. The bioassays results reveal that part of the target compounds exhibit better activities against Xanthomonas oryzae pv. Oryzae (Xoo) and Xanthomonas axonopodis pv. Citri (Xac) than positive controls thiodiazole copper and bismerthiazol (≥ 57.4%). Among them, the inhibitory rates of (2-(2-methoxyphenyl)-7-methoxy-4-oxo-4H-chromen-3-yl)diethyl phosphonate (2b), (2-(2-methoxyphenyl)-7-ethoxy-4-oxo-4H-chromen-3-yl)diethyl phosphonate (2f) and (2-(3,4-dimethoxyphenyl)-7-ethoxy-4-oxo-4H-chromen-3-yl)diethyl phosphonate (2m) reached 92.8%, 87.7% and 88.3% against Xoo at a concentration of 100 µg/mL, respectively. In addition, the inhibitory rates of (2-(4-fluorophenyl)-7-ethoxy-4-oxo-4H-chromen-3-yl)diethyl phosphonate (2h) and (2-(p-tolyl)-7-ethoxy-4-oxo-4H-chromen-3-yl)diethyl phosphonate (2k) reached 85.1% and 71.7% against Xac at a concentration of 100 µg/mL, respectively.

Synthesis and antibacterial and antiviral activities of myricetin derivatives containing a 1,2,4-triazole Schiff base

“…In fact, in Chinese herbal medicines, avonoids are very important active substances. Flavonoids have antibacterial, 5,6 antiviral, 7,8 antitumor, 9 and antioxidant 10 activities. Myricetin (3 0 ,4 0 ,5 0 ,3,5,7-hexahy-droxyavonol, Myr), similar to bayanone, is an important polyphenol avonoid that is widely found in many plants.…”

Novel Phosphorylated Penta-1,4-dien-3-one Derivatives: Design, Synthesis, and Biological Activity

“…Because the phosphorus–carbon bond of phosphonate derivatives is not susceptible to enzymatic degradation, they possess improved cell permeability, a lipophilic nature, and good physiological stability [ 26 , 27 ]. In a previous study from our group, we synthesized a series of phosphorylated flavonoid derivatives ( Figure 2 ), most of which exhibited excellent antibacterial activities [ 21 , 28 ]. However, relatively few reports were conducted on plant antiviral activities.…”

Design, Synthesis, and Biological Activity of Novel penta-1,4-dien-3-one Derivatives Containing a <em>H</em>-phosphonate Scaffold

“…H-phosphonate and its derivatives possess a wide range of biological activities [17][18][19][20][21][22][23] and are therefore widely employed as plant virucides, bactericides, fungicides, herbicides, and plant growth regulators. Because the phosphorus-carbon bond of phosphonates is not susceptible to enzymatic degradation, it possesses more cell permeability, a lipophilic nature, and good physiological stability [24,25].…”