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

In the H-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.

Heck- and Suzuki-coupling approaches to novel hydroquinone inhibitors of calcium ATPase.

In this study, we explored Heck- and Suzuki-coupling methodology to modify the template 2,5-di--butylhydroquinone (BHQ, ), an inhibitor of the enzyme sarco/endoplasmic reticulum calcium ATPase (SERCA). We found that by utilizing Suzuki coupling, we could successfully attach a six-carbon tether to BHQ that terminated in a leucine moiety to obtain target . Similar to related compounds based on the structure of the natural product thapsigargin, displayed inhibitory potency against SERCA activity.

Design, synthesis, and biological evaluation of hydroquinone derivatives as novel inhibitors of the sarco/endoplasmic reticulum calcium ATPase.

Analogues of the compound 2,5-di-tert-butylhydroquinone (BHQ) are capable of inhibiting the enzyme sarco/endoplasmic reticulum ATPase (SERCA) in the low micromolar and submicromolar concentration ranges. Not only are SERCA inhibitors valuable research tools, but they also have potential medicinal value as agents against prostate cancer. This study describes the synthesis of 13 compounds representing several classes of BHQ analogues, such as hydroquinones with a single aromatic substituent, symmetrically and unsymmetrically disubstituted hydroquinones, and hydroquinones with omega-amino acid tethers attached to their hydroxyl groups.

Molecular determinants of sarco/endoplasmic reticulum calcium ATPase inhibition by hydroquinone-based compounds.

The ion transport activity of the sarco/endoplasmic reticulum calcium ATPase (SERCA) is specifically and potently inhibited by the small molecule 2,5-di-tert-butylhydroquinone (BHQ). In this study, we investigated the relative importance of the nature and position of BHQ's four substituents for enzyme inhibition by employing a combination of experimental and computational techniques. The inhibitory potencies of 21 commercially available or synthesized BHQ derivatives were determined in ATPase activity assays, and 11 compounds were found to be active.