201. Cascade Transformations of 1-R-Ethynyl-9,10-anthraquinones with Amidines: Expanding Access to Isoaporphinoid Alkaloids
- Author
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Sergey Francevich Vasilevsky, Ol’ga Leonidovna Krivenko, Irina Vasilievna Sorokina, Dmitry Sergeevich Baev, Tatyana Genrikhovna Tolstikova, and Igor V. Alabugin
- Subjects
alkynes ,amidines ,cyclization ,2-R-7H-dibenzo[de,h]quinolin-7-ones ,anti-inflammatory activity ,Organic chemistry ,QD241-441 - Abstract
The interaction of acetamidine and phenylamidine with peri-R-ethynyl-9,10-anthraquinones in refluxing n-butanol leads to the formation of cascade transformations products: addition/elimination/cyclization―2-R-7H-dibenzo[de,h]quinolin-7-ones and(or) 2-R-3-aroyl-7H-dibenzo[de,h]quinolin-7-ones. The anti-inflammatory and antitumor properties of the new 2-R-7H-dibenzo[de,h]quinolin-7-ones were investigated in vivo, in vitro, and in silico. The synthesized compounds exhibit high anti-inflammatory activity at dose 20 mg/kg (intraperitoneal injection) in the models of exudative (histamine-induced) and immunogenic (concanavalin A-induced) inflammation. Molecular docking data demonstrate that quinolinones can potentially intercalate into DNA similarly to the antitumor drug doxorubicin.
- Published
- 2021
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