Construction of sulfur-containing compounds with anti-cancer stem cell activity using thioacrolein derived from garlic based on nature-inspired scaffolds
| Autor: | Tasusada Yoshida, Taichi Yoneda, Takahiro Matsumoto, Tomoe Ohta, Daisuke Imahori, Tetsushi Watanabe, Hisashi Matsuda, Naoto Kojima, Seikou Nakamura |
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| Rok vydání: | 2022 |
| Předmět: |
Diene
Cell Survival Antineoplastic Agents Biochemistry chemistry.chemical_compound Tumor Cells Cultured Humans Molecule Ajoene Acrolein Physical and Theoretical Chemistry Garlic Cytotoxicity Density Functional Theory Molecular Structure Sulfur Compounds Allicin Plant Extracts Organic Chemistry Regioselectivity Silyl enol ether Combinatorial chemistry chemistry Neoplastic Stem Cells Chemical stability Drug Screening Assays Antitumor |
| Zdroj: | Organic & Biomolecular Chemistry. 20:196-207 |
| ISSN: | 1477-0539 1477-0520 |
| DOI: | 10.1039/d1ob01992a |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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