Synthesis, antioxidant activity, antimicrobial activity, and fluorescent property of furan-/pyridine aminophosphonate derivatives

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Eight new furan-/pyridine aminophosphonate derivatives A1–A4 and B1–B4 were synthesized by a one-pot Kabachnik–Fields reaction of diethyl phosphite with furfural (pyridine-2-aldehyde) and four different amines with phenyl group. The structures of the synthesized compounds were elucidated by the spectral analysis using 1H,13C and 31P NMR as well as IR and FTMS. The results of antioxidant experiments showed that compounds A3 and B3 display intermediate antioxidant activity at the concentration range of 1–100 µM and IC50 value of 2.02 µM and 2.87 µM, respectively. According to the results of antimicrobial experiments, these eight compounds showed differently strong anti-fungal and antibacterial activity in the concentration range of 125–1000 μg/mL. Fluorescent experiments revealed that the emission wavelength range of A1–A4 and B1–B4 is between 650 nm and 750 nm at the concentration of 1 × 10−5 mol/L. A single crystal of B2 was selected for X-ray crystallography. The compound crystallizes in a monoclinic system with space group C2/c.