Through-space H-F coupling in a series of 4-substituted-1H-1,2,3-triazoles.

In the 1H-NMR spectra of a series of N-1 substituted 4-substituted-1H-1,2,3-triazoles that have been prepared, the lone heterocyclic ring hydrogen (H-5) appears as a singlet in all cases except those compounds that contain a 2-fluorophenyl moiety at Position 4. In those cases, H-5 is a doublet with J ~3.7 Hz. Based on computational chemistry results and geometric considerations, we attribute this splitting to through-space H-F coupling.

Synthesis and PGE2 inhibitory activity of novel diarylheptanoids.

Prostaglandin E2 (PGE2) is a lipid mediator of inflammation and its inhibition has become a popular drug target due to its harmful physiological roles. Diarylheptanoids are one class of compounds that have shown successful inhibition of PGE2. This paper reports the synthesis and PGE2 inhibitory activity of a series of analogues of a naturally occurring diarylheptanoid. The most efficacious compounds were examined for dose-dependent PGE2 inhibition. Among several promising compounds, the lead candidate exhibited an IC50 value of 0.56 ng/µL or 1.7 µM with no detectable toxicity at the highest dose of 10 ng/µL.