204847-08-5Relevant articles and documents
2-furanyl-quinoline-4-formamide compound and application thereof
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Paragraph 0018-0020, (2021/02/06)
The invention discloses a 2-furanyl-quinoline-4-formamide compound and application thereof, and the structural formula of the 2-furanyl-quinoline-4-formamide compound is shown as a formula (4) in thespecification, wherein R1 is selected from H, halogen or
Discovery of Potent Small-Molecule SIRT6 Activators: Structure-Activity Relationship and Anti-Pancreatic Ductal Adenocarcinoma Activity
Chen, Xiuli,Sun, Weining,Huang, Shenzhen,Zhang, Hailin,Lin, Guifeng,Li, Hui,Qiao, Jingxin,Li, Linli,Yang, Shengyong
, p. 10474 - 10495 (2020/11/02)
SIRT6 activation is thought to be a promising target for the treatment of many diseases, particularly cancer. Herein, we report the discovery of a series of new small-molecule SIRT6 activators. Structure-activity relationship analyses led to the identific
Oxidative Reactivities of 2-Furylquinolines: Ubiquitous Scaffolds in Common High-Throughput Screening Libraries
Olson, Margaret E.,Abate-Pella, Daniel,Perkins, Angela L.,Li, Ming,Carpenter, Michael A.,Rathore, Anurag,Harris, Reuben S.,Harki, Daniel A.
, p. 7419 - 7430 (2015/10/05)
High-throughput screening (HTS) was employed to discover APOBEC3G inhibitors, and multiple 2-furylquinolines (e.g., 1) were found. Dose-response assays with 1 from the HTS sample, as well as commercial material, yielded similar confirmatory results. Interestingly, freshly synthesized and DMSO-solubilized 1 was inactive. Repeated screening of the DMSO aliquot of synthesized 1 revealed increasing APOBEC3G inhibitory activity with age, suggesting that 1 decomposes into an active inhibitor. Laboratory aging of 1 followed by analysis revealed that 1 undergoes oxidative decomposition in air, resulting from a [4 + 2] cycloaddition between the furan of 1 and 1O2. The resulting endoperoxide then undergoes additional transformations, highlighted by Baeyer-Villager rearrangements, to deliver lactam, carboxylic acid, and aldehyde products. The endoperoxide also undergoes hydrolytic opening followed by further transformations to a bis-enone. Eight structurally related analogues from HTS libraries were similarly reactive. This study constitutes a cautionary tale to validate 2-furylquinolines for structure and stability prior to chemical optimization campaigns.