关于二苯并呋喃酮中乙烯砜基侧链对其生物活性的作用。
On the role of the vinylsulfoxide side chain of dirchromone towards its bioactivities.
机构信息
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.
出版信息
Org Biomol Chem. 2020 Dec 21;18(47):9700-9705. doi: 10.1039/d0ob01783c. Epub 2020 Nov 24.
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.
为了阐明其独特的乙烯砜侧链在其细胞毒性和抗菌性能方面的关键作用，特别是依赖于硫的存在和氧化态，我们制备了二氢查耳酮类似物。二氢查耳酮与半胱胺的反应表现出一种出人意料的迈克尔加成体行为，其中亚甲基砜部分消除，硫原子发生氧化还原转化，这可能涉及二氢查耳酮在细胞内的作用模式。
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