Semisynthesis of Antitrypanosomal p-Quinone Analog Possesing the Komaroviquinone Pharmacophore

Yutaka Aoyagi; Koji Fujiwara; Yoshinao Takahashi; Reiko Yano; Yukio Hitotsuyanagi; Koichi Takeya; Ritsuo Aiyama; Takeshi Matsuzaki; Shusuke Hashimoto; Aki Nishihara-Tsukashima; Miyuki Namatame; Aki Ishiyama; Masato Iwatsuki; Kazuhiko Otoguro; Haruki Yamada; Satoshi Ōmura

doi:10.1248/cpb.c21-00998

Notes

Semisynthesis of Antitrypanosomal p-Quinone Analog Possesing the Komaroviquinone Pharmacophore

Yutaka Aoyagi , Koji Fujiwara, Yoshinao Takahashi, Reiko Yano, Yukio Hitotsuyanagi, Koichi Takeya, Ritsuo Aiyama, Takeshi Matsuzaki, Shusuke Hashimoto, Aki Nishihara-Tsukashima, Miyuki Namatame, Aki Ishiyama, Masato Iwatsuki, Kazuhiko Otoguro, Haruki Yamada, Satoshi Ōmura

Author information

Yutaka Aoyagi Corresponding author
College of Pharmacy, Kinjo Gakuin University
Koji Fujiwara
School of Pharmacy, Tokyo University of Pharmacy & Life Sciences
Yoshinao Takahashi
School of Pharmacy, Tokyo University of Pharmacy & Life Sciences
Reiko Yano
College of Pharmacy, Kinjo Gakuin University
Yukio Hitotsuyanagi
School of Pharmacy, Tokyo University of Pharmacy & Life Sciences
Koichi Takeya
School of Pharmacy, Tokyo University of Pharmacy & Life Sciences
Ritsuo Aiyama
Yakult Central Institute
Takeshi Matsuzaki
Yakult Central Institute
Shusuke Hashimoto
Yakult Central Institute
Aki Nishihara-Tsukashima
Ōmura Satoshi Memorial Institute, Kitasato University
Miyuki Namatame
Ōmura Satoshi Memorial Institute, Kitasato University
Aki Ishiyama
Ōmura Satoshi Memorial Institute, Kitasato University
Masato Iwatsuki
Ōmura Satoshi Memorial Institute, Kitasato University
Kazuhiko Otoguro
Ōmura Satoshi Memorial Institute, Kitasato University
Haruki Yamada
Ōmura Satoshi Memorial Institute, Kitasato University
Satoshi Ōmura
Ōmura Satoshi Memorial Institute, Kitasato University

Keywords: semisynthesis, demethylsalvicanol, antitrypanosomal activity, komaroviquinone analog, Perovskia abrotanoides

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Supplementary material

2022 Volume 70 Issue 4 Pages 300-303

DOI https://doi.org/10.1248/cpb.c21-00998

Details

Abstract

A p-quinone analog having the komaroviquinone pharmacophore fused with a more conformationally flexible cycloheptane ring, was semisynthesized from natural demethlsalvicanol isolated from Perovskia abrotanoides via four steps in 26% overall yield. The IC₅₀ for the antitrypanosomal activity of the analog was 0.55 µM.

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