•Asymmetric synthesis of novel triazole derivatives.•Good antiviral activities compared with the Ribavirin.•The most potent compounds 10 and 43 showed highly antiviral activity.•The potential mechanism of action has been investigated.In this study, forty-four chiral triazole derivatives have been prepared via asymmetric synthesis, and which has been successfully characterized by typical spectroscopic techniques including 1H NMR, 13C NMR, EI-MS, elemental analysis and optical rotations. Their in vitro antiviral activities against EV71 and CVB3 were fully investigated in cell-based assays. It was observed that 13 synthetic triazole derivatives inhibited the CPE of EV71 on RD cells, with EC50S in the 5.3–15.9 μg/ml range and corresponding SIs of 4.0–27.6, while 17 triazole derivatives showed antiviral activities against CVB3, with EC50S in the 4.7–15.1 μg/ml range and the corresponding SIs of 3.7–14.5. In addition, in some cases, the respective enantiomers showed significantly selective inhibitory effect against EV71, most notably for the enantiomers 9(R) and 10(S), 42(R) and 43(S), which presented an obvious activity difference. The most potential molecules are the compounds 10 and 43 with S-configuration, and which exhibit good SI values compared with the control Ribavirin.In this study, forty-four chiral triazole derivatives have been synthesized via asymmetric synthesis, and their in vitro antiviral activities against EV71 and CVB3 were fully investigated in cell-based assays, and the results indicated the most potential molecules are the compounds 10 and 43 with S-configuration, and which exhibit good TI values compared with the control Ribavirin.Download high-res image (518KB)Download full-size image

•Receptors AR-1, AR-4, and AR-6 can be utilized as a colorimetric chemosensor for detection of AcO− or F− anions.•Receptors AR-1 and AR-4 can naked-eye detect of F− and AcO−.•Receptors exhibit low detection limit when the concentration of receptors are 2 × 10− 5 mol/L.Several acylthioureas have been synthesized to develop colorimetric sensors for detection of biologically important anions. UV–vis titration experiments indicated that the absorbance values have a good linear relationship with concentration of anions when the anions were added in AR-1, AR-4 and AR-6 sensor molecules. The detection limit to AcO− and F− is 5 × 10− 6 mol/L when the concentration of receptors are 2 × 10− 5 mol/L. Especially, compounds AR-1 and AR-4, decorated with strong electron-withdrawing NO2 substituent, showed augmented anion sensing properties, being capable of naked-eye detecting of F− and AcO− when the water content is lower than 15%. The recognition details of anion sensing were also assessed using 1H NMR technique and confirmed that the basic anions induced deprotonation of N–H.Thioureas have been synthesized to develop colorimetric sensors for detection of biologically important anions. The recognition details of anion sensing were assessed using UV–vis titration, IR, and 1H NMR techniques.

Three series of novel peptidomimetics bearing the tryptamine moiety were designed, synthesized, and evaluated for their inhibition activities against cell proliferation. According to the preliminary studies on cytotoxic activities, some of the newly prepared compounds (Ia–k, IIa–d, IIIa–g) displayed significant inhibition activities against human hepatoma cancer (HepG2 and Huh-7), and human melanoma (A875) cell lines compared with the control 5-fluorouracil. Especially, compounds Ih and Ij exhibited obvious inhibition activities (Ih IC50 = 4.88 ± 0.78 μg mL−1; Ij IC50 = 6.60 ± 1.20 μg mL−1) against 5-fluorouracil-resistant human hepatocellular carcinoma (BEL-7402/5-FU) cell lines.

In the present study, a simple and inexpensive method for the simultaneous determination of 22 pesticides in aquatic vegetables by HPLC spectrum analyses with diode array detector (HPLC–DAD) is established. The proposed method is also applied for the analyses of pesticides residues in water chestnut, lotus root, and wild rice shoots, and the results indicate that this method could meet the requirements for simultaneous determination of the pesticides. The calibration showed good linearity for all the tested pesticides with correlation coefficients of 0.9936–0.9994. Recoveries for the studied 22 pesticides at their three spiked concentration levels in water chestnut ranged from 73.5 to 108.3 %, with relative standard deviations of 1.7–12.5 %. Limits of quantitation for the analytes were estimated to range between 0.01 and 10.00 mg kg−1.

A series of novel chiral esters derived from tetrafluorobenzyl alcohol were designed and prepared via asymmetric synthesis. The target molecules have been identified on the basis of analytical spectra data. All newly synthesized compounds have been screened their potential insecticidal activity against Plutella xylostella compared with those of fenvalerate and d-trans-phenothrin by standard method, and the respective pairs of enantiomers (3-B1-R/S, 3-C1-R/S, 3-D1-R/S) indicated significantly different activities.A series of novel chiral esters derived from tetrafluorobenzyl alcohol were designed and distereoselectively synthesized, and the respective pairs of enantiomers (3-B1-R/S, 3-C1-R/S, 3-D1-R/S) indicated significantly different activities.

Based on the salicylic acid backbone, three highly sensitive and selective colorimetric chemosensors with an acylthiourea binding unit have been designed, synthesized and characterized. These chemosensors have been utilized for selective recognition of fluoride anions in dry DMSO solution by typical spectroscopic titration techniques. Furthermore, the obtained chemosensors AR1–3 have shown naked-eye sensitivity for detection of biologically important fluoride ion over other anions in solution.Graphical abstractHighlights► Receptors AR1–3 can be utilized as a colorimetric chemosensor for detection of F− anion. ► Receptors AR1–3 are novel salicylic acid-oriented thiourea-type receptors. ► Receptors AR1–3 showed excellent selectivity toward F− over the other competitive anions.

A series of N-nitrourea derivatives bearing various cycloalkyl were conveniently obtained via three steps including nitration, carbamic chlorination, and aminolysis reactions. The structures of all newly synthesized compounds were elucidated and confirmed by IR, 1H NMR, 13C NMR, and elemental analysis. The preliminary bioassay indicated that the target compounds exhibited moderate herbicidal activity against Amaranthus albus and Sorghum sudanense. However, some of the title compounds presented high plant growth regulating activity against rice.

Twenty-two novel N-nitro-N′-substituted phenyl-N-(2,6-dibromo-4-fluorophenyl)urea derivatives were designed and synthesized via a simple and convenient BTC ‘one-pot’ procedure using DMAP as the catalyst. The structures of all newly synthesized compounds were confirmed by IR, 1H NMR, and elemental analysis, and a part has been identified by 13C NMR. The preliminary bioassay indicates that the target compounds possesses moderate herbicidal activity against Sorghum sudanense. However, some of the title compounds presented high plant growth regulating activity against rape.

A series of substituted-nicotinyl thiourea derivatives containing pyrimidine ring were synthesized in good to excellent yield using PEG-400 as solid–liquid phase transfer catalyst under ultrasonic irradiation. The structures of all newly synthesized compounds were elucidated and confirmed by IR, 1H NMR and elemental analysis. The preliminary biological tests show that some of the target compounds present good inhibitory activities against the root and stalk of dicotyledon plants and are safe for monocotyledon plants.

Highlights•The novel N-nitroacetamides derived from 2,4-D have been conveniently obtained.•The novel N-nitroacetamides derivatives exhibited good herbicidal activities.•In vitro inhibition activities and molecular docking indicated that these compounds might target AHAS enzyme.A series of novel N-nitroacetamides derived from 2,4-dichlorophenoxyacetic acid (2,4-D, a important plant growth regulator) have been conveniently obtained via multi-step reactions including oxidation, bromination, nitration, chlorination, and acylation reactions. All the structures of newly prepared compounds were thoroughly characterized by satisfied IR, 1H NMR, and 13C NMR spectrums. The herbicidal activity and plant growth regulating activities of target compounds were also assessed. The preliminary bioassay results showed that these novel N-nitroacetamide derivatives exhibited good herbicidal activity against both dicotyledonous and monocotyledonous weeds. Meanwhile, some of the target compounds displayed high plant growth regulating activity against Rice at the dosage of 0.1 mg/L. The further in vitro inhibition activity against acetohydroxyacid synthase (AHAS) enzyme and molecular docking indicated that AHAS might be the primary target site for these newly synthesized compounds.A series of novel N-nitroacetamides derivatives targeting AHAS enzyme have been obtained and evaluated, and some of the target compounds displayed good activities at the dosage of 0.1 mg/L.Download full-size image

A series of chiral β-arylalkyl-1H-1,2,4-triazole derivatives were prepared and both their in vitro antifungal activities against Penicillium digitatum and binding activity toward CYP51 protein of P. digitatum (PdCYP51) were tested. In general, the in vitro inhibitory activities of R- and S-enantiomers were in good agreement with the corresponding binding activities in cultured cells. Furthermore, the preliminary molecular docking modeling of representative compounds are described to provide more insight into their stereoselective interaction, as well as further rationalize the observations of the activities of chiral azoles as demethylase inhibitors for defense against postharvest pathogens.Graphical abstractMolecular docking results show that the S-isomer more favorably fits the active site of the cytochrome. The more tightly the compounds bind to the PdCYP51, the greater their antifungal activity.Download full-size imageResearch highlights► Excellent in vitro antifungal activities against P. digitatum. ► Potential demethylase inhibitors for defense against postharvest pathogens. ► Respective enantiomers showed significantly different inhibitory activities. ► Chiral triazoles present obvious stereoselective interaction with enzyme.