33647-76-6Relevant articles and documents
Design, Synthesis, and Phenotypic Profiling of Pyrano-Furo-Pyridone Pseudo Natural Products
Christoforow, Andreas,Wilke, Julian,Binici, Aylin,Pahl, Axel,Ostermann, Claude,Sievers, Sonja,Waldmann, Herbert
supporting information, p. 14715 - 14723 (2019/09/06)
Natural products (NPs) inspire the design and synthesis of novel biologically relevant chemical matter, for instance through biology-oriented synthesis (BIOS). However, BIOS is limited by the partial coverage of NP-like chemical space by the guiding NPs. The design and synthesis of “pseudo NPs” overcomes these limitations by combining NP-inspired strategies with fragment-based compound design through de novo combination of NP-derived fragments to unprecedented compound classes not accessible through biosynthesis. We describe the development and biological evaluation of pyrano-furo-pyridone (PFP) pseudo NPs, which combine pyridone- and dihydropyran NP fragments in three isomeric arrangements. Cheminformatic analysis indicates that the PFPs reside in an area of NP-like chemical space not covered by existing NPs but rather by drugs and related compounds. Phenotypic profiling in a target-agnostic “cell painting” assay revealed that PFPs induce formation of reactive oxygen species and are structurally novel inhibitors of mitochondrial complex I.
The binary reagent PhI(OAc)2-Mg(ClO4)2: a SET induced ring enlargement of furan derivatives into pyranones
De Mico,Margarita,Piancatelli
, p. 3553 - 3556 (2007/10/02)
The binary reagent PhI(OAc)2-Mg(ClO4)2 is very efficient for a high conversion of (2-furyl)-1-alcohols into puranones. The reaction mechanism can be explained in terms of a SET process, with the generation of a cation radical as key intermediate.
