Cascade Transformations of 1-R-Ethynyl-9,10-anthraquinones with Amidines: Expanding Access to Isoaporphinoid Alkaloids

Molecules

Igor V. Alabugin¹  Irina Vasilievna Sorokina²  Dmitry Sergeevich Baev²  Tatyana Genrikhovna Tolstikova²  Ol’ga Leonidovna Krivenko³  Sergey Francevich Vasilevsky³ 

[1] Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL 32306, USA;N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Acad. Lavrent’eva, 630090 Novosibirsk, Russia;V.V. Voevodsky Institute of Chemical Kinetics and Combustion, Siberian Branch of the Russian Academy of Science, 630090 Novosibirsk, Russia;

关键词: alkynes;    amidines;    cyclization;    2-R-7H-dibenzo[de,h]quinolin-7-ones;    anti-inflammatory activity;   

DOI  :  10.3390/molecules26226883

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown