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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Autores principales: Sergey Francevich Vasilevsky, Ol’ga Leonidovna Krivenko, Irina Vasilievna Sorokina, Dmitry Sergeevich Baev, Tatyana Genrikhovna Tolstikova, Igor V. Alabugin
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Publicado: MDPI AG 2021
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Acceso en línea:https://doaj.org/article/d1dd199f47804d2db0eef77d0bdd4ec6
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spelling oai:doaj.org-article:d1dd199f47804d2db0eef77d0bdd4ec62021-11-25T18:28:07ZCascade Transformations of 1-R-Ethynyl-9,10-anthraquinones with Amidines: Expanding Access to Isoaporphinoid Alkaloids10.3390/molecules262268831420-3049https://doaj.org/article/d1dd199f47804d2db0eef77d0bdd4ec62021-11-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/22/6883https://doaj.org/toc/1420-3049The 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.Sergey Francevich VasilevskyOl’ga Leonidovna KrivenkoIrina Vasilievna SorokinaDmitry Sergeevich BaevTatyana Genrikhovna TolstikovaIgor V. AlabuginMDPI AGarticlealkynesamidinescyclization2-R-7<i>H</i>-dibenzo[<i>de,h</i>]quinolin-7-onesanti-inflammatory activityOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6883, p 6883 (2021)
institution DOAJ
collection DOAJ
language EN
topic alkynes
amidines
cyclization
2-R-7<i>H</i>-dibenzo[<i>de,h</i>]quinolin-7-ones
anti-inflammatory activity
Organic chemistry
QD241-441
spellingShingle alkynes
amidines
cyclization
2-R-7<i>H</i>-dibenzo[<i>de,h</i>]quinolin-7-ones
anti-inflammatory activity
Organic chemistry
QD241-441
Sergey Francevich Vasilevsky
Ol’ga Leonidovna Krivenko
Irina Vasilievna Sorokina
Dmitry Sergeevich Baev
Tatyana Genrikhovna Tolstikova
Igor V. Alabugin
Cascade Transformations of 1-R-Ethynyl-9,10-anthraquinones with Amidines: Expanding Access to Isoaporphinoid Alkaloids
description 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.
format article
author Sergey Francevich Vasilevsky
Ol’ga Leonidovna Krivenko
Irina Vasilievna Sorokina
Dmitry Sergeevich Baev
Tatyana Genrikhovna Tolstikova
Igor V. Alabugin
author_facet Sergey Francevich Vasilevsky
Ol’ga Leonidovna Krivenko
Irina Vasilievna Sorokina
Dmitry Sergeevich Baev
Tatyana Genrikhovna Tolstikova
Igor V. Alabugin
author_sort Sergey Francevich Vasilevsky
title Cascade Transformations of 1-R-Ethynyl-9,10-anthraquinones with Amidines: Expanding Access to Isoaporphinoid Alkaloids
title_short Cascade Transformations of 1-R-Ethynyl-9,10-anthraquinones with Amidines: Expanding Access to Isoaporphinoid Alkaloids
title_full Cascade Transformations of 1-R-Ethynyl-9,10-anthraquinones with Amidines: Expanding Access to Isoaporphinoid Alkaloids
title_fullStr Cascade Transformations of 1-R-Ethynyl-9,10-anthraquinones with Amidines: Expanding Access to Isoaporphinoid Alkaloids
title_full_unstemmed Cascade Transformations of 1-R-Ethynyl-9,10-anthraquinones with Amidines: Expanding Access to Isoaporphinoid Alkaloids
title_sort cascade transformations of 1-r-ethynyl-9,10-anthraquinones with amidines: expanding access to isoaporphinoid alkaloids
publisher MDPI AG
publishDate 2021
url https://doaj.org/article/d1dd199f47804d2db0eef77d0bdd4ec6
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