論文雑誌「Chemical and Pharmaceutical Bulletin」のカバーピクチャーを制作しました［北里大学］
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日本薬学会発行の学術雑誌 Chemical and Pharmaceutical Bulletin
2022年4月号に選ばれました。
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北里大学
薬学部
長光亨先生
薬学部
長光亨先生
Journal
Chemical and Pharmaceutical Bulletin
April 2022, VOL 70 No.4 Link
April 2022, VOL 70 No.4 Link
Synthesis and Evaluation of Habiterpenol Analogs
Miyuki Konya, Shiho Arima, Daiki Lee, Masaki Ohtawa, Kenta Shimoyama, Takashi Fukuda, Ryuji Uchida, Hiroshi Tomoda, Noriyuki Yamaotsu, Nobutada Tanaka, Tohru Nagamitsu
Habiterpenol is a G2 checkpoint inhibitor isolated from the culture broth of Phytohabitans sp. 3787_5. Here, we report the synthesis of new habiterpenol analogs through the total synthesis process of habiterpenol and evaluating the analogs for G2 checkpoint inhibitory activity. We investigated two different synthetic approaches for total synthesis, with intramolecular conjugate addition and Ti(III)-mediated radical cyclization as key reactions. Although the former was unsuccessful, the latter reaction facilitated stereoselective total synthesis and determination of the absolute configuration of habiterpenol. The extension of these chemistries to a structure–activity relationship (SAR) study gave new habiterpenol analogs, which could not be derived from natural habiterpenol and only be synthesized by applying the total synthesis. Therefore, this study provides important insights into SAR studies of habiterpenol.
Link
Miyuki Konya, Shiho Arima, Daiki Lee, Masaki Ohtawa, Kenta Shimoyama, Takashi Fukuda, Ryuji Uchida, Hiroshi Tomoda, Noriyuki Yamaotsu, Nobutada Tanaka, Tohru Nagamitsu
Habiterpenol is a G2 checkpoint inhibitor isolated from the culture broth of Phytohabitans sp. 3787_5. Here, we report the synthesis of new habiterpenol analogs through the total synthesis process of habiterpenol and evaluating the analogs for G2 checkpoint inhibitory activity. We investigated two different synthetic approaches for total synthesis, with intramolecular conjugate addition and Ti(III)-mediated radical cyclization as key reactions. Although the former was unsuccessful, the latter reaction facilitated stereoselective total synthesis and determination of the absolute configuration of habiterpenol. The extension of these chemistries to a structure–activity relationship (SAR) study gave new habiterpenol analogs, which could not be derived from natural habiterpenol and only be synthesized by applying the total synthesis. Therefore, this study provides important insights into SAR studies of habiterpenol.
Link
