116176-92-2Relevant articles and documents
Rhodium(III)-Catalyzed Regioselective C?H Allylation and Prenylation of Indoles at C4-Position
Zhang, Shang-Shi,Liu, Yan-Zhi,Zheng, Yi-Chuan,Xie, Hui,Chen, Shao-Yong,Song, Jia-Lin,Shu, Bing
supporting information, p. 64 - 70 (2021/11/03)
Herein, Rh(III)-catalyzed C4-selective C?H allylation and prenylation of indoles by using a weak carbonyl coordination directing group have been reported. By employing 5-methylene-1,3-dioxan-2-ones, 4-vinyl-1,3-dioxolan-2-ones and 2-methyl-2,3-butadiene as scalable cross-coupling partners, these divergent synthesis protocols proceed smoothly under redox-neutral reaction conditions, delivering various allylated and prenylated indoles in moderate to satisfied yields. This transformation exhibits high functional-groups compatibility and broad substrate scope. Scale-up experiment and mechanistic studies were also accomplished. (Figure presented.).
1,2,4-Oxadiazole Topsentin Analogs with Antiproliferative Activity against Pancreatic Cancer Cells, Targeting GSK3β Kinase
Carbone, Daniela,Parrino, Barbara,Cascioferro, Stella,Pecoraro, Camilla,Giovannetti, Elisa,Di Sarno, Veronica,Musella, Simona,Auriemma, Giulia,Cirrincione, Girolamo,Diana, Patrizia
, p. 537 - 554 (2020/12/01)
A new series of topsentin analogs, in which the central imidazole ring of the natural lead was replaced by a 1,2,4-oxadiazole moiety, was efficiently synthesized. All derivatives were pre-screened for antiproliferative activity against the National Cancer Institute (NCI-60) cell lines panel. The five most potent compounds were further investigated in various pancreatic ductal adenocarcinoma (PDAC) cell lines, including SUIT-2, Capan-1, and Panc-1 cells, eliciting EC50 values in the micromolar and sub-micromolar range, associated with significant reduction of cell migration. These remarkable results might be explained by the effects of these new topsentin analogues on epithelial-to-mesenchymal transition markers, including SNAIL-1/2 and metalloproteinase-9. Moreover, flow cytometric analysis after Annexin V-FITC and propidium iodide staining demonstrated that these derivatives enhanced apoptosis of PDAC cells. Keeping with these data, the PathScan intracellular signaling and ELISA array revealed cleavage of caspase-3 and PARP and a significant inhibition of GSK3β phosphorylation, suggesting this kinase as a potential downstream target of our novel compounds. This was further supported by a specific assay for the evaluation of GSK3β activity, showing IC50 values for the most active compounds against this enzyme in the micromolar range.
The palladium-catalyzed direct C3-cyanation of indoles using acetonitrile as the cyanide source
Feng, Kejun,Li, Qiang,Li, Yuanhua,Liu, Bifu,Liu, Min,Zhou, Yongbo
supporting information, p. 6108 - 6114 (2020/10/21)
The ligand-free palladium-catalyzed C3-cyanation of indoles via direct C-H functionalization was achieved. This protocol, utilizing CH3CN as a green and readily available cyanide source, produced the desired products in moderate to good yields through transition-metal-catalyzed C-CN bond cleavage. This journal is
