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Construction of sulfur-containing compounds with anti-cancer stem cell activity using thioacrolein derived from garlic based on nature-inspired scaffolds.
Yoneda, Taichi; Kojima, Naoto; Matsumoto, Takahiro; Imahori, Daisuke; Ohta, Tomoe; Yoshida, Tatsusada; Watanabe, Tetsushi; Matsuda, Hisashi; Nakamura, Seikou.
Affiliation
  • Yoneda T; Kyoto Pharmaceutical University, 1 Misasagi-Shichono-cho, Yamashina-ku, Kyoto 607-8412, Japan. naka@mb.kyoto-phu.ac.jp.
  • Kojima N; Kyoto Pharmaceutical University, 1 Misasagi-Shichono-cho, Yamashina-ku, Kyoto 607-8412, Japan. naka@mb.kyoto-phu.ac.jp.
  • Matsumoto T; Kyoto Pharmaceutical University, 1 Misasagi-Shichono-cho, Yamashina-ku, Kyoto 607-8412, Japan. naka@mb.kyoto-phu.ac.jp.
  • Imahori D; Kyoto Pharmaceutical University, 1 Misasagi-Shichono-cho, Yamashina-ku, Kyoto 607-8412, Japan. naka@mb.kyoto-phu.ac.jp.
  • Ohta T; Faculty of Pharmaceutical Sciences, Nagasaki International University, 2825-7 Huis Ten Bosch-Cho, Sasebo, Nagasaki 859-3298, Japan.
  • Yoshida T; Faculty of Pharmaceutical Sciences, Nagasaki International University, 2825-7 Huis Ten Bosch-Cho, Sasebo, Nagasaki 859-3298, Japan.
  • Watanabe T; Kyoto Pharmaceutical University, 1 Misasagi-Shichono-cho, Yamashina-ku, Kyoto 607-8412, Japan. naka@mb.kyoto-phu.ac.jp.
  • Matsuda H; Kyoto Pharmaceutical University, 1 Misasagi-Shichono-cho, Yamashina-ku, Kyoto 607-8412, Japan. naka@mb.kyoto-phu.ac.jp.
  • Nakamura S; Kyoto Pharmaceutical University, 1 Misasagi-Shichono-cho, Yamashina-ku, Kyoto 607-8412, Japan. naka@mb.kyoto-phu.ac.jp.
Org Biomol Chem ; 20(1): 196-207, 2021 12 22.
Article in En | MEDLINE | ID: mdl-34878480
Sulfur-containing compounds, such as cyclic compounds with a vinyl sulfane structure, exhibit a wide range of biological activities including anticancer activity. Therefore, the development of efficient strategies to synthesize such compounds is a remarkable achievement. We have developed a unique approach for the rapid and modular preparation of nature-inspired cyclic and acyclic sulfur-containing compounds using thioacrolein, a naturally occurring chemically unstable intermediate. We constructed thiopyranone derivatives through the regioselective sequential double Diels-Alder reaction of thioacrolein produced by allicin, a major component in garlic, and two molecules of silyl enol ether as the diene partner. The cytotoxicity toward cancer stem cells of the thiopyranones was equal to or higher than that of (Z)-ajoene (positive control) derived from garlic, and the thiopyranones had higher chemical stability than (Z)-ajoene.
Subject(s)

Full text: 1 Database: MEDLINE Main subject: Sulfur Compounds / Neoplastic Stem Cells / Acrolein / Plant Extracts / Garlic / Antineoplastic Agents Language: En Journal: Org Biomol Chem Year: 2021 Type: Article Affiliation country: Japan

Full text: 1 Database: MEDLINE Main subject: Sulfur Compounds / Neoplastic Stem Cells / Acrolein / Plant Extracts / Garlic / Antineoplastic Agents Language: En Journal: Org Biomol Chem Year: 2021 Type: Article Affiliation country: Japan