Cascade Transformations of 1-R-Ethynyl-9,10-anthraquinones with Amidines: Expanding Access to Isoaporphinoid Alkaloids
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-7<i>H</i>-dibenzo[<i>de</i>,<i>h</i>]quinolin-7-ones an...
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| Main Authors: | , , , , , |
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| Format: | article |
| Language: | EN |
| Published: |
MDPI AG
2021
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| Subjects: | |
| Online Access: | https://doaj.org/article/d1dd199f47804d2db0eef77d0bdd4ec6 |
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| Summary: | 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-7<i>H</i>-dibenzo[<i>de</i>,<i>h</i>]quinolin-7-ones and(or) 2-R-3-aroyl-7<i>H</i>-dibenzo[<i>de</i>,<i>h</i>]quinolin-7-ones. The anti-inflammatory and antitumor properties of the new 2-R-7H-dibenzo[<i>de,h</i>]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. |
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