A series of novel racemic otobain derivatives was designed and synthesised using 2-piperonyl-1,3-dithianes in the conjugate addition–alkylation to 5H-furan-2-one, followed by cationic cyclisation. All the synthesised compounds were consequently evaluated for their anticancer activity against several human cancers in vitro. The efficacy of the most active compound 27g was comparable with etoposide, with IC50 values ranging from 1.06 μM to 4.16 μM in different cancer cell lines. Notably, compound 27g strongly induced cell cycle arrest and increased the expression of mitosis-specific markers MPM-2 and phosphorylated histone H3, but it did not trigger cell apoptosis. Further a colony formation assay showed that compound 27g effectively inhibited the anchor growth of lung cancer cells in a dose-dependent manner. More importantly, compound 27g at 40 mg kg−1 significantly suppressed tumour volume (P < 0.01) and tumour weight (P < 0.05) in a human lung cancer cell xenograft mouse model without causing systematic toxicity in mice. Our findings indicated that compound 27g has significant potential for further drug development.

Using an acetone precipitation method, crude (S)-hydroxynitrile lyase [(S)-MeHNL] was separated from Munihot esculenta (cassava) leaves, and used directly as biocatalyst to catalyze asymmetric cyanohydrination and produce cyanohydrins with enantiomeric purities (⩾90% ee) significantly greater than those previously reported. The use of a water/i-Pr2O system with an enzyme, NaCN, and appropriate amounts of acetic acid is crucial in improving the stereoselectivity of cyanohydrin formation by minimizing the non-enzymatic reaction and the racemization of the chiral products. The proposed isolation method for crude (S)-MeHNL has a high value because of its simplicity, and low cost as well as the high activity of the crude (S)-MeHNL.(S)-(−)-1-Cyano-1-(phenyl)methyl acetateC10H9NO297% ee[α]D25=-6.2 (c 0.10, CHCl3)Source of chirality: enzymatic catalysisAbsolute configuration: (S)(S)-(+)-1-Cyano-1-(4-methylphenyl)methyl acetateC11H11NO291% ee[α]D25=+6.4 (c 0.8, CHCl3)Source of chirality: enzymatic catalysisAbsolute configuration: (S)(S)-(−)-1-Cyano-1-(3-methylphenyl)methyl acetateC11H11NO285% ee[α]D25=-21.5 (c 0.5, CHCl3)Source of chirality: enzymatic catalysisAbsolute configuration: (S)(S)-(−)-1-Cyano-1-(2-methoxyphenyl)methyl acetateC11H11NO390% ee[α]D25=-18.4 (c 0.12, CHCl3)Source of chirality: enzymatic catalysisAbsolute configuration: (S)(S)-(−)-1-Cyano-1-(3-methoxyphenyl)methyl acetateC11H11NO396% ee[α]D25=-5.1 (c 0.12, CHCl3)Source of chirality: enzymatic catalysisAbsolute configuration: (S)(S)-(+)-1-Cyano-1-(4-methoxyphenyl)methyl acetateC11H11NO391% ee[α]D25=+6.4 (c 0.08, CHCl3)Source of chirality: enzymatic catalysisAbsolute configuration: (S)(S)-(+)-1-Cyano-1-(4-chlorophenyl)methyl acetateC10H8NO2Cl96% ee[α]D25=+10.7 (c 0.11, CHCl3)Source of chirality: enzymatic catalysisAbsolute configuration: (S)(S)-(+)-1-Cyano-1-[3,4-(methylenedioxy)-phenyl]methyl acetateC11H9NO497% ee[α]D25=+14.4 (c 0.14, CHCl3)Source of chirality: enzymatic catalysisAbsolute configuration: (S)(R)-(+)-1-Cyano-1-(2-furyl)methyl acetateC8H7NO390% ee[α]D25=+15.3 (c 0.09, CHCl3)Source of chirality: enzymatic catalysisAbsolute configuration: (R)(R)-(+)-1-Cyano-1-(2-thienyl)methyl acetateC8H7NO2S94% ee[α]D25=+9.1 (c 0.09, CHCl3)Source of chirality: enzymatic catalysisAbsolute configuration: (R)(R)-(+)-1-Cyano-1-[2-(5-methylthienyl)]methyl acetateC9H9NO2S96% ee[α]D25=+14.4 (c 1.2, CHCl3)Source of chirality: enzymatic catalysisAbsolute configuration: (R)(R)-(+)-1-Cyano-1-[2-(5-bromothienyl)]methyl acetateC8H6NO2SBr86% ee[α]D25=+15.7 (c 2.6, CHCl3)Source of chirality: enzymatic catalysisAbsolute configuration: (R)(S)-(+)-1-Cyano-1-(3-thienyl)methyl acetateC8H7NO2S88% ee[α]D25=+10.8 (c 0.1, CHCl3)Source of chirality: enzymatic catalysisAbsolute configuration: (S)(S)-(−)-PentanenitrileC7H11NO287% ee[α]D25=-56.8 (c 0.08, CHCl3)Source of chirality: enzymatic catalysisAbsolute configuration: (S)

A series of novel monohalovinylated pyrethroids are designed and synthesized to replace one halo atom with a hydrogen atom on the double bond of dihalopyrethroids. Bioassays indicate that some of the synthesized compounds, such as 3j and 1j, exhibit high insecticidal activities against mosquitoes (Culex pipiens pallens), oriental armyworms (Mythimna separata), alfalfa aphids (Aphis medicagini), and carmine spider mites (Tetranychus cinnabarinus). Photolytic results of E-cis-1j suggest that monohalovinylated pyrethroids are photodegraded more easily than compound 12.

Two methods of nucleophilic fluorination to prepare α-fluoroacetophenones from α-bromoacetophenones by using KF with PEG-400 or TBAF with ZnF2 are described. On the fundamental of nucleophilic fluorination, a novel method of one-pot fluorination to prepare α-fluoroacetophenones directly from acetophenones in DES was developed.Two methods of nucleophilic fluorination to prepare α-fluoroacetophenones from α-bromoacetophenones by using KF with PEG-400 or TBAF with ZnF2 are described. On the fundamental of nucleophilic fluorination, a novel method of one-pot fluorination to prepare α-fluoroacetophenones directly from acetophenones in DES was developed.

New processes that can selectively prepare α-mono or α,α-dichloro ketones and β-ketoesters using 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) are reported. Using silica gel as the catalyst and methanol as the solvent and heating for 1 h under reflux, α-monochlorinated products were selectively obtained in 86–98% yield. However using a deep eutectic solvent (choline chloride: p-TsOH = 1:1) as the solvent and stirring for 45 min at room temperature, α,α-dichlorinated products were selectively obtained in 86–95% yield.

The synthesis of polyfluorinated benzyl alcohol from pentafluorobenzoic acid has been developed. An economical and effective direct reduction method of polyfluorobenzoic acid by zinc borohydride is described.The synthesis of polyfluorinated benzyl alcohol from pentafluorobenzoic acid has been developed. An economical and effective direct reduction method of polyfluorobenzoic acid by zinc borohydride is described.

A series of novel racemic otobain derivatives was designed and synthesised using 2-piperonyl-1,3-dithianes in the conjugate addition–alkylation to 5H-furan-2-one, followed by cationic cyclisation. All the synthesised compounds were consequently evaluated for their anticancer activity against several human cancers in vitro. The efficacy of the most active compound 27g was comparable with etoposide, with IC50 values ranging from 1.06 μM to 4.16 μM in different cancer cell lines. Notably, compound 27g strongly induced cell cycle arrest and increased the expression of mitosis-specific markers MPM-2 and phosphorylated histone H3, but it did not trigger cell apoptosis. Further a colony formation assay showed that compound 27g effectively inhibited the anchor growth of lung cancer cells in a dose-dependent manner. More importantly, compound 27g at 40 mg kg−1 significantly suppressed tumour volume (P < 0.01) and tumour weight (P < 0.05) in a human lung cancer cell xenograft mouse model without causing systematic toxicity in mice. Our findings indicated that compound 27g has significant potential for further drug development.