10.1007/s00706-012-0792-7
The study focuses on the asymmetric synthesis of novel chiral 1,2- and 1,3-diols through the reduction of corresponding 1,2-diketones and 1,3-diketones using an oxazaborolidine–BH3 catalyst. The research successfully synthesized seven chiral 1,2-diols and six chiral 1,3-diols, with five of the starting diketones, four racemic 1,2-diols, five chiral 1,2-diols, and two chiral 1,3-diols being identified as new compounds. The methodology applied, the oxazaborolidine–BH3 reduction, was a first-time application to these types of diketones. The study also involved the synthesis of the corresponding racemic 1,2- and 1,3-diols using NaBH4 for the determination of enantiomeric excess (ee) values through chiral resolution on high-performance liquid chromatography (HPLC) and gas chromatography (GC). The newly synthesized chiral compounds were characterized using various analytical techniques, including infrared (IR), proton and carbon-13 nuclear magnetic resonance (1H and 13C NMR), mass spectrometry (MS), and elemental analysis. The relationship between the structure of the diketone and the yield, diastereoselectivity, and enantiomeric excess was also discussed, providing insights into the stereoselective reduction process.
10.1021/acs.jafc.9b00837
This study focuses on the development of chitinase inhibitors as a potential strategy for pest control, specifically targeting the chitinase enzyme (Of ChtI) from the Asian corn borer (Ostrinia furnacalis), which is crucial for the insect's molting process. The researchers utilized a pocket-based lead optimization strategy to synthesize and evaluate a series of compounds based on a 4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate scaffold. The lead compound 1 was optimized by introducing various nonpolar groups at the 6-position, resulting in compound 8, which exhibited the most promising inhibitory activity with a K value of 0.71 μM. The study combines computational modeling, molecular docking, and experimental bioassays to investigate the structure-activity relationships of these compounds, providing valuable insights for the design of more effective chitinase inhibitors as green pesticides.
10.1002/poc.435
The research focuses on the tautomeric preferences of 2-phenylhydrazones of 1,3-diphenyl-1,2,3-trione in chloroform solution, as detected by 15N NMR chemical shifts. The study aims to understand whether the substituent in the phenylhydrazone moiety influences the tautomeric preference and the transmission of the substituent effect within the molecules. Experiments involved the synthesis of compounds through the coupling of benzenediazonium ion to 1,3-diphenyl-1,3-propanedione, followed by purification via recrystallization from ethanol. The synthesized compounds were then analyzed using 1H, 13C, and 15N NMR spectroscopy, with chemical shifts referenced to tetramethylsilane (TMS) and nitromethane. Additionally, ab initio calculations at the HF/B3LYP level of theory with GIAO-HF/DFT method were conducted to calculate the chemical shifts of carbon atoms, and X-ray crystallography was used to detect the tautomer in the crystal state. The study found that the ketohydrazone tautomer is significantly favored over its proton-transfer products, and this tautomer was also detected in the crystalline state, indicating that the additional carbonyl group or substituent does not affect the tautomeric and configurational preferences.
F+
