67200-34-4Relevant academic research and scientific papers
Design, synthesis, and characterization of oxadiazolopyrazine analogs with application as anticancer agents
Chen, Wei-Chia,Chen, Chia-Ling,Chang, Tzu-Ting,Hsieh, Feng-Chun,Chen, Wei-Sheng,Li, Wen-Shan
, p. 375 - 387 (2021/12/23)
Here, we describe the synthesis and evaluation of a class of cell-permeable indeno-oxadiazolopyrazine analogs as the anticancer agents. A new and facile approach to the synthesis of substituted analogs of indeno-oxadiazolopyrazine is illustrated. We find that the designed indeno-oxadiazolopyrazines, 3, 4, 10, 11, 15, and 16, act as potent anticancer agents compared to camptothecin, topoisomerase I inhibitor. These observations suggest that the electron-donating group (methoxy) at the C-5, C-6, and C-8 positions or electron-withdrawing group (fluoro) at the C-6 and C-7 positions on the A ring of indeno-oxadiazolopyrazines is required for antiproliferative activities against MDA-MB-231, BT549, and MCF7 cell lines.
METHODS AND COMPOSITIONS OF SUBSTITUTED 5H-[1,2,5]OXADIAZOLO[3',4':5,6] PYRAZIONO[2,3-B]INDOLE ANALOGS AS INHIBITORS OF BETA-CATENIN/T-CELL FACTOR PROTEIN-PROTEIN INTERACTIONS
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Paragraph 00291, (2016/12/07)
In one aspect, the invention relates to substituted 5H-[1,2,5]oxadiazolo [3',4':5,6]pyrazino[2,3-b]indole analogues, derivatives thereof, and related compound; synthetic methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of treating disorders, e.g., various tumors and cancers, associated with a β-catenin/T-cell factor interaction dysfunction using the compounds and compositions. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.
Discovery of Selective Small-Molecule Inhibitors for the β-Catenin/T-Cell Factor Protein-Protein Interaction through the Optimization of the Acyl Hydrazone Moiety
Catrow, J. Leon,Zhang, Yongqiang,Zhang, Min,Ji, Haitao
, p. 4678 - 4692 (2015/06/25)
Acyl hydrazone is an important functional group for the discovery of bioactive small molecules. This functional group is also recognized as a pan assay interference structure. In this study, a new small-molecule inhibitor for the β-catenin/Tcf protein-protein interaction (PPI), ZINC02092166, was identified through AlphaScreen and FP assays. This compound contains an acyl hydrazone group and exhibits higher inhibitory activities in cell-based assays than biochemical assays. Inhibitor optimization resulted in chemically stable derivatives that disrupt the β-catenin/Tcf PPI. The binding mode of new inhibitors was characterized by site-directed mutagenesis and structure-activity relationship studies. This series of inhibitors with a new scaffold exhibits dual selectivity for β-catenin/Tcf over β-catenin/cadherin and β-catenin/APC PPIs. One derivative of this series suppresses canonical Wnt signaling, downregulates the expression of Wnt target genes, and inhibits the growth of cancer cells. This compound represents a solid starting point for the development of potent and selective β-catenin/Tcf inhibitors (Chemical Equation).
Ionic liquids - Advanced reaction media for organic synthesis
Ignat'ev, Nikolai V.,Schulte, Michael,Koppe, Karsten,Barthen, Peter,Zlotin, Sergei G.,Makhova, Nina N.,Sheremetev, Aleksei B.,Valente, Anabela A.
scheme or table, p. 1205 - 1216 (2011/09/16)
The advantages in the application of ionic liquids as reaction media in organic synthesis, i.e., in the preparation of chromane derivatives, substituted pyrazines, 4-aminofuran-2(5H)-ones, or in bromination of Levulinic acid or dehydration of alcohols, saccharides, and polysaccharides, have been demonstrated on several examples. Ionic liquids with Bronsted acidity have been shown to possess catalytic activity and provide access to convenient technologies for the preparation of various useful compounds. Copyright Merck KGaA.
