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...
Guardado en:
Autores principales: | , , , , , |
---|---|
Formato: | article |
Lenguaje: | EN |
Publicado: |
MDPI AG
2021
|
Materias: | |
Acceso en línea: | https://doaj.org/article/d1dd199f47804d2db0eef77d0bdd4ec6 |
Etiquetas: |
Agregar Etiqueta
Sin Etiquetas, Sea el primero en etiquetar este registro!
|
id |
oai:doaj.org-article:d1dd199f47804d2db0eef77d0bdd4ec6 |
---|---|
record_format |
dspace |
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 |
work_keys_str_mv |
AT sergeyfrancevichvasilevsky cascadetransformationsof1rethynyl910anthraquinoneswithamidinesexpandingaccesstoisoaporphinoidalkaloids AT olgaleonidovnakrivenko cascadetransformationsof1rethynyl910anthraquinoneswithamidinesexpandingaccesstoisoaporphinoidalkaloids AT irinavasilievnasorokina cascadetransformationsof1rethynyl910anthraquinoneswithamidinesexpandingaccesstoisoaporphinoidalkaloids AT dmitrysergeevichbaev cascadetransformationsof1rethynyl910anthraquinoneswithamidinesexpandingaccesstoisoaporphinoidalkaloids AT tatyanagenrikhovnatolstikova cascadetransformationsof1rethynyl910anthraquinoneswithamidinesexpandingaccesstoisoaporphinoidalkaloids AT igorvalabugin cascadetransformationsof1rethynyl910anthraquinoneswithamidinesexpandingaccesstoisoaporphinoidalkaloids |
_version_ |
1718411160970067968 |