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

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 Ca2+ release (PCR) from sarcoplasmic reticulum (SR) in mouse skeletal muscle without affecting Ca2+-induced Ca2+ release (CICR).

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 providing an easy access to RI-free photoaffinity probes possessing biaryl structure. By using this method, a novel diazido-functionalized dantrolene analog with selective inhibitory effect on physiological Ca2+ release from sarcoplasmic reticulum in mouse skeletal muscle was prepared.Figure optionsDownload as PowerPoint slide