Facile synthesis of diazido-functionalized biaryl compounds as radioisotope-free photoaffinity probes by Suzuki-Miyaura coupling

Bioorg Med Chem. 2009 Mar 15;17(6):2490-6. doi: 10.1016/j.bmc.2009.01.070. Epub 2009 Feb 5.

Abstract

Suzuki-Miyaura coupling of 3-azido-5-(azidomethyl)phenylboronic acid pinacol ester with various aryl bromides affords corresponding diazido-functionalized biaryl compounds in good yields. This approach provides an easy access to radioisotope-free photoaffinity probes possessing biaryl structure. By using this method, we prepared a novel diazido-functionalized dantrolene analog, which showed selective inhibitory effect on physiological Ca(2+) release (PCR) from sarcoplasmic reticulum (SR) in mouse skeletal muscle without affecting Ca(2+)-induced Ca(2+) release (CICR).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azides / chemistry*
  • Calcium / chemistry
  • Magnetic Resonance Spectroscopy
  • Photoaffinity Labels*
  • Radioisotopes
  • Spectrometry, Mass, Electrospray Ionization
  • Spectrometry, Mass, Fast Atom Bombardment

Substances

  • Azides
  • Photoaffinity Labels
  • Radioisotopes
  • Calcium