177348-97-9Relevant academic research and scientific papers
Systematic Diversity-Oriented Synthesis of Reduced Flavones from γ-Pyrones to Probe Biological Performance Diversity
Gerlach, Erica M.,Korkmaz, Melissa A.,Pavlinov, Ivan,Gao, Qiwen,Aldrich, Leslie N.
, p. 1536 - 1545 (2019)
Diversity-oriented synthesis (DOS) has historically focused on the development of small-molecule collections with considerable chemical diversity with the hypothesis that chemical diversity will lead to diverse biological activities. We took a systematic approach to DOS to develop a focused library of reduced flavones from ?-pyrones with diversity of appendage, stereochemistry, and chemical properties to determine which features of small molecules are most predictive of biological performance diversity. The effects of these systematic modifications on biodiversity were determined using Cell Painting and cytotoxicity assays to compare the results of multiple methods of assessment. We observed that a greater fraction of sp3 hybridized atoms (fsp3) does not always lead to enhanced biodiversity, that stereochemistry and appendage diversity both contribute to biodiversity, and that lipophilicity of the pyrone class of compounds correlates with biodiversity. These results will contribute to the development of a general algorithm to predict which chemical features should be considered during the synthesis of DOS libraries to create biological performance-diverse collections of small molecules for probe and drug discovery.
Synthesis and reactions of reduced flavones
Groundwater, Paul W.,Hibbs, David E.,Hursthouse, Michael B.,Nyerges, Miklos
, p. 163 - 169 (2007/10/03)
The cycloadditions of a series of 4H-pyran-4-ones 3c-e with electron-rich dienes 11a,b to give reduced flavones 12 is described. The subsequent reactions of these reduced flavones with HCl, trifluoroacetic anhydride, ethyl anthranilate 19a and anthranilon
