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One-step synthesis of dicarboxamides through Pd-catalysed aminocarbonylation with diamines as N-nucleophiles
synthetic methods
carbonylation
dicarboxamides
medicinal chemistry
antitumor agents
An efficient one-step synthetic strategy was used to prepare a set of dicarboxamides through palladium-catalysed aminocarbonylation of iodoalkenyl and iodoaryl compounds, with use of various alkyl- and aryldiamines as N-nucleophiles. The isolated yields of the dicarboxamides depended significantly on the iodo substrate and diamine structures, as well as on the reaction conditions, the best one (ca. 70 %) being achieved with 1-iodocyclohexene as substrate and 1,4-diaminobutane as nucleophile, at 100 °C and 30 bar of CO. When iodobenzene was used as model aryl halide, the highest yield of the target dibenzamides (ca. 65 %) was obtained with 1,4-diaminobenzene as coupling amine, at 100 °C and 10 bar of CO. Preliminary studies on their in vitro cytotoxicity against human lung carcinoma A549 cells showed N,N′-(butane-1,4-diyl)dibenzamide and androst-16-ene-based dicarboxamides to be the most efficient cytotoxic agents, with IC50 values of approximately 40 μM.
cris.lastimport.scopus | 2024-04-07T16:24:29Z | |
cris.lastimport.wos | 2024-04-09T22:53:09Z | |
dc.abstract.en | An efficient one-step synthetic strategy was used to prepare a set of dicarboxamides through palladium-catalysed aminocarbonylation of iodoalkenyl and iodoaryl compounds, with use of various alkyl- and aryldiamines as N-nucleophiles. The isolated yields of the dicarboxamides depended significantly on the iodo substrate and diamine structures, as well as on the reaction conditions, the best one (ca. 70 %) being achieved with 1-iodocyclohexene as substrate and 1,4-diaminobutane as nucleophile, at 100 °C and 30 bar of CO. When iodobenzene was used as model aryl halide, the highest yield of the target dibenzamides (ca. 65 %) was obtained with 1,4-diaminobenzene as coupling amine, at 100 °C and 10 bar of CO. Preliminary studies on their in vitro cytotoxicity against human lung carcinoma A549 cells showed N,N′-(butane-1,4-diyl)dibenzamide and androst-16-ene-based dicarboxamides to be the most efficient cytotoxic agents, with IC50 values of approximately 40 μM. | pl |
dc.affiliation | Wydział Chemii : Zakład Chemii Nieorganicznej | pl |
dc.contributor.author | Carrilho, Rui M. B. | pl |
dc.contributor.author | Almeida, Ana R. | pl |
dc.contributor.author | Kiss, Mercédesz | pl |
dc.contributor.author | Kollár, László | pl |
dc.contributor.author | Skoda-Földes, Rita | pl |
dc.contributor.author | Dąbrowski, Janusz - 200579 | pl |
dc.contributor.author | Moreno, Maria José S. M. | pl |
dc.contributor.author | Pereira, Mariette M. | pl |
dc.date.accessioned | 2015-07-02T10:20:44Z | |
dc.date.available | 2015-07-02T10:20:44Z | |
dc.date.issued | 2015 | pl |
dc.description.number | 8 | pl |
dc.description.physical | 1840-1847 | pl |
dc.description.volume | 2015 | pl |
dc.identifier.doi | 10.1002/ejoc.201403444 | pl |
dc.identifier.eissn | 1099-0690 | pl |
dc.identifier.issn | 1434-193X | pl |
dc.identifier.uri | http://ruj.uj.edu.pl/xmlui/handle/item/11198 | |
dc.language | eng | pl |
dc.language.container | eng | pl |
dc.rights.licence | bez licencji | |
dc.subject.en | synthetic methods | pl |
dc.subject.en | carbonylation | pl |
dc.subject.en | dicarboxamides | pl |
dc.subject.en | medicinal chemistry | pl |
dc.subject.en | antitumor agents | pl |
dc.subtype | Article | pl |
dc.title | One-step synthesis of dicarboxamides through Pd-catalysed aminocarbonylation with diamines as N-nucleophiles | pl |
dc.title.journal | European Journal of Organic Chemistry | pl |
dc.type | JournalArticle | pl |
dspace.entity.type | Publication |