Analogs of dirchromone were prepared to shed light on the pivotal role of its peculiar vinylsulfoxide side chain towards its cytotoxic and antimicrobial properties, especially dependant upon the presence and oxidation state of sulfur. The reaction of dirchromone with cysteamine revealed a surprising Michael acceptor behavior with elimination of the methylsulfinyl moiety and redox transformation of the sulfur atom that could be involved in the mode of action of dirchromone within cells.
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http://dx.doi.org/10.1039/d0ob01783c | DOI Listing |
Org Biomol Chem
December 2020
Chaire de recherche sur les agents anticancéreux d'origine naturelle, Laboratoire d'analyse et de séparation des essences végétales (LASEVE), Département des Sciences Fondamentales, Université du Québec à Chicoutimi, 555, boulevard de l'Université, Chicoutimi, Québec G7H 2B1, Canada.
Analogs of dirchromone were prepared to shed light on the pivotal role of its peculiar vinylsulfoxide side chain towards its cytotoxic and antimicrobial properties, especially dependant upon the presence and oxidation state of sulfur. The reaction of dirchromone with cysteamine revealed a surprising Michael acceptor behavior with elimination of the methylsulfinyl moiety and redox transformation of the sulfur atom that could be involved in the mode of action of dirchromone within cells.
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