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 Ca(2+) release (PCR) from sarcoplasmic reticulum (SR) in mouse skeletal muscle without affecting Ca(2+)-induced Ca(2+) release (CICR).
Hosoya
Takamitsu
T
Department of Biological Information, Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology and SORST, Japan Science and Technology Agency, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan. thosoya@bio.titech.ac.jp
Inoue
Atsushi
A
Hiramatsu
Toshiyuki
T
Aoyama
Hiroshi
H
Ikemoto
Takaaki
T
Suzuki
Masaaki
M
D001386:Azides / Q000737:chemistry*; D002118:Calcium / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D019920:Photoaffinity Labels; D011868:Radioisotopes; D021241:Spectrometry, Mass, Electrospray Ionization; D016339:Spectrometry, Mass, Fast Atom Bombardment
D001386:Azides; D019920:Photoaffinity Labels; D011868:Radioisotopes; D002118:Calcium