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Short Paper | Special issue | Vol 99, No. 2, 2019, pp.1366-1387
Published online, 3rd December, 2018
DOI: 10.3987/COM-18-S(F)76
Divergent Synthesis of Photoaffinity Probe Candidates by Click Reactions of Azido-Substituted Aryltrifluoromethyldiazirines

Kenji Watanabe, Junpei Tsuda, Hidenori Ochiai, Takashi Niwa, and Takamitsu Hosoya*

*Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU), 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan

Abstract

Two types of azido-substituted aryltrifluoromethyldiazirine units have been designed and prepared for the divergent synthesis of photoaffinity probe (PAP) candidates. Using these azides, various aryltrifluoromethyldiazirine derivatives have been rendered easily synthesizable by several click reactions, as well as the Staudinger reduction affording the corresponding aniline. The triazole-conjugated aryltrifluoromethyldiazirine derivatives prepared in this study showed normal photoreactivity compared with those reported previously. These results indicate the utility of these azido-substituted aryltrifluoromethyldiazirine units for development of PAPs for target identification of bioactive compounds.