Several novel 3-(aryl)benzothieno[2,3-c]pyran-1-ones (tricyclic lactones) were prepared either by a tandem one-pot Sonogashira coupling and intramolecular cyclization, reacting the 3-bromobenzo[b]thiophene-2-carboxylic acid with arylacetylenes, or by Sonogashira coupling of the methyl 3-bromobenzo[b]thiophene-2-carboxylate or the methyl 3-bromo-6-methoxybenzo[b]thiophene-2-carboxylate with arylacetylenes followed by an electrophilic intramolecular cyclization using iodine or TFA in two separate steps. The Sonogashira products and the tricyclic lactones obtained were evaluated for their capacity to inhibit the in vitro growth of three human tumor cell lines, MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer) and SF-268 (CNS cancer). Most of the compounds showed a high growth inhibitory effect on all the tested cell lines, with GI(50) values in the muM range. A structure-activity relationship was established for the Sonogashira products and for the tricyclic lactones, namely related to the presence and position of substituents (OMe and/or F) in the benzothiophene moiety or in the phenyl ring.
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http://dx.doi.org/10.1016/j.ejmech.2008.11.002 | DOI Listing |
Org Biomol Chem
December 2024
School of Chemistry and Chemical Engineering, Tianjin University of Technology, Tianjin, 300384, China.
Herein, we report an enantioselective Pd/Cu-catalyzed sequential Heck/Sonogashira coupling reaction of electron-rich enamides with terminal alkynes as substrates. This transformation proceeds smoothly to afford 3-propargyl isoindolinone derivatives bearing quaternary stereogenic centers in moderate to good yields (43-77% yield) and good to excellent enantioselectivity (up to 93% ee). Functional groups such as halogen atoms (F, Cl, and Br), thienyl, and silyl moieties are tolerated well.
View Article and Find Full Text PDFOrg Lett
December 2024
Leibniz-Institut für Katalyse e.V., Albert-Einstein-Straße 29a, 18059 Rostock, Germany.
Herein, we developed a mild and efficient palladium-catalyzed carbonylative Sonogashira coupling of aryl thianthrenium salts with aliphatic alkynes and benzyl acetylene toward alkynones and furanones. Various desired products were prepared in good yields with broad functional group tolerance including the bromide group. In the case of using benzyl acetylene, the corresponding furanones can be obtained in good yields under the same conditions with two molecules of CO inserted.
View Article and Find Full Text PDFMolecules
November 2024
Institut für Organische Chemie und Makromolekulare Chemie, Mathematisch-Naturwissenschaftliche Fakultät, Heinrich-Heine-Universität Düsseldorf, Universitätsstrasse 1, D-40225 Düsseldorf, Germany.
Org Lett
December 2024
Albert-Ludwigs-Universität Freiburg, Institute of Organic Chemistry, Albertstr. 21, 79104 Freiburg, Germany.
In this report, we describe Pd-catalyzed cascade reactions in which two internal alkynes undergo two -carbocarbonation reactions, leading to new carbon-carbon bonds across the emerging double bonds. The resulting vinyl Pd intermediate being obtained after two carbopalladations is involved in either terminating Suzuki or Sonogashira reactions leading to either highly substituted butadienes or hexadienynes. A variety of different precursors as well as boronic acids and alkynes, respectively, were employed, yielding a broad spectrum of the corresponding products in yields of up to 82%.
View Article and Find Full Text PDFMolecules
October 2024
Department of Chemistry, Dankook University, Cheonan 31116, Republic of Korea.
Cysteine plays a crucial role in the development of an efficient copper-catalyst system, where its thiol group serves as a strong anchoring site for metal coordination. By immobilizing copper onto cysteine-modified, polydopamine-coated magnetite particles, this advanced catalytic platform exhibits exceptional stability and catalytic activity. Chemical modification of the polydopamine (PDA) surface with cysteine enhances copper salt immobilization, leading to the formation of the FeO@PDA-Cys@Cu platform.
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