The application of fluorescent method to metal ions detection features high sensitivity, simple operation and real‐time monitoring. A 2,7‐dihydroxynaphthalene‐functionalized dimethyl glycoluril (called clip 1) was synthesized, using a relatively simple method. And it is fully characterized by 1H NMR, 13C NMR, HR‐MS and single crystal X‐ray diffraction. The recognition properties of molecular clip 1 were analyzed systematically toward several metal ions using fluorescence spectroscopy, and it was found that molecular clip 1 is selective and sensitive to Fe3+. At the same time, the clip 1 shows good anti‐interference ability when other metal ions existed. The limit detection of Fe3+ is 3×10−7M. The fluorescence of clip 1 was quenched apparently by Fe3+, which was speculated to be caused by ligand–metal charge transfer mechanism (LMCT). As a new fluorescence probe for Fe3+ ion, it may expanded the application of glycoluril molecular clips.
Novel nereistoxin derivatives containing phosphonate were synthesized and characterized via 31P, 1H and 13C NMR and HRMS. The anticholinesterase activity of the synthesized compounds was evaluated on human acetylcholinesterase (AChE) using the in vitro Ellman method. Most of the compounds exhibited good inhibition of acetylcholinesterase. All of these compounds were selected to assess their insecticidal activity (in vivo) against Mythimna separata Walker, Myzus persicae Sulzer and Rhopalosiphum padi. Most of the tested compounds displayed potent insecticidal activity against these three species. Compound 7f displayed good activity against all three insect species, showing LC50 values of 136.86 μg/mL for M. separata, 138.37 μg/mL for M. persicae and 131.64 μg/mL for R. padi. Compound 7b had the highest activity against M. persicae and R. padi, with LC50 values of 42.93 μg/mL and 58.19 μg/mL, respectively. Docking studies were performed to speculate the possible binding sites of the compounds and explain the reasons for the activity of the compounds. The results showed that the compounds had lower binding energies with AChE than with the acetylcholine receptor (AchR), suggesting that compounds are more easily bound with AChE.
A new glycoluril derivative‐1H, 4H, 5H, 8H‐2, 3a, 4a, 6, 7a, 8a‐hexaazacyclopenta[def]fluorene‐4, 8‐dione, hexahydro‐2, 6‐bis(phenylmethyl) (3) is strategically designed and synthesized through the reaction between glycoluril, formaldehyde and benzylamine with the optimized molar ratio of 1:6:2. Compound 3 is fully characterized by 1H NMR, 13C NMR, IR, MS and X‐ray single crystal diffraction. Reduction of compound 3 delivers a potential precursor‐imidazo[4, 5‐d]imidazole, octahydro‐hexahydro‐2, 6‐bis(phenylmethyl) (4) for the synthesis of novel nitramine explosives (i.e. bicyclo‐HMX and bi‐RDX). The nitration and hydrolysis of compound 4 are investigated in detail and three ring‐opened molecules N, 2, 4‐trinitro‐benzenemethanamine (8a), N, 2‐dinitro‐benzenemethanamine (8b) and N‐methylene‐benzenemethanamine (9) are obtained.
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