- Highly efficient monophosphine-based catalyst for the palladium-catalyzed Suzuki-Miyaura reaction of heteroaryl halides and heteroaryl boronic acids and esters
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A highly active and efficient catalyst system derived from a palladium precatalyst and monophosphine ligands 1 or 2 for the Suzuki-Miyaura cross-coupling reaction of heteroaryl boronic acids and esters has been developed. This method allows for the preparation of a wide variety of heterobiaryls in good to excellent yields and displays a high level of activity for the coupling of heteroaryl chlorides as well as hindered aryl and heteroaryl halides. Specific factors that govern the efficacy of the transformation for certain heterocyclic motifs were also investigated.
- Billingsley, Kelvin,Buchwald, Stephen L.
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- New 6- and 7-heterocyclyl-1H-indole derivatives as potent tubulin assembly and cancer cell growth inhibitors
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We designed new 3-arylthio- and 3-aroyl-1H-indole derivatives 3–22 bearing a heterocyclic ring at position 5, 6 or 7 of the indole nucleus. The 6- and 7-heterocyclyl-1H-indoles showed potent inhibition of tubulin polymerization, binding of colchicine to tubulin and growth of MCF-7 cancer cells. Compounds 13 and 19 inhibited a panel of cancer cells and the NCI/ADR-RES multidrug resistant cell line at low nanomolar concentrations. Compound 13 at 50 nM induced 77% G2/M in HeLa cells, and at 20 nM caused 50% stable arrest of mitosis. As an inhibitor of HepG2 cells (IC50 = 20 nM), 13 was 4-fold superior to 19. Compound 13 was a potent inhibitor of the human U87MG glioblastoma cells at nanomolar concentrations, being nearly one order of magnitude superior to previously reported arylthioindoles. The present results highlight 13 as a robust scaffold for the design of new anticancer agents.
- La Regina, Giuseppe,Bai, Ruoli,Coluccia, Antonio,Naccarato, Valentina,Famiglini, Valeria,Nalli, Marianna,Masci, Domiziana,Verrico, Annalisa,Rovella, Paola,Mazzoccoli, Carmela,Da Pozzo, Eleonora,Cavallini, Chiara,Martini, Claudia,Vultaggio, Stefania,Dondio, Giulio,Varasi, Mario,Mercurio, Ciro,Hamel, Ernest,Lavia, Patrizia,Silvestri, Romano
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p. 283 - 297
(2018/05/22)
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- Conjugated oligomers with thiophene and indole moieties: Synthesis, photoluminescence and electrochromic performances
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Two series of thiophene oligomers and terthiophene oligomers consisting of both thiophene and indole moieties have been synthesized. They have same excitation-dependent photoluminescence characteristics, but different bandgaps and absorption behaviors, which relates to the number and denseness of indoles in the conjugated oligomers and the length of alkyl chains on indole moiety due to varied the π-π stacking interaction of conjugated structures in the as-prepared oligomers. A simple electrochromic device based on such a conjugated oligomer displays a novel four-color electrochromism from red to yellow, green and puce with the increased potential and possesses good environmental and redox stability. Such conjugated oligomer also exhibits high sensitivity and selectivity for Zn2+detection.
- Dong, Ben,Li, Baoyan,Cao, Yi,Meng, Xinlei,Yan, Han,Ge, Shusheng,Lu, Yun
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- SYNTHESIS OF 5-ARYLATED INDOLES VIA PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF 5-INDOLYLBORONIC ACID WITH ARYL AND HETEROARYL HALIDES
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Palladium(0)-catalyzed cross-coupling reaction of 5-indolylboronic acid with various aryl and heteroaryl halides results in regioselective formation of 5-arylated indoles in good yields.
- Yang, Youhua,Martin, Arnold R.
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p. 1395 - 1398
(2007/10/02)
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