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

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

Bioorganic & medicinal chemistry (2009-02-24)
Takamitsu Hosoya, Atsushi Inoue, Toshiyuki Hiramatsu, Hiroshi Aoyama, Takaaki Ikemoto, Masaaki Suzuki
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).

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
1-Aminohydantoin hydrochloride, 98%