1361317-33-0Relevant academic research and scientific papers
Synthesis of azaphilone-based chemical libraries
Achard, Mathieu,Beeler, Aaron B.,Porco, John A.
scheme or table, p. 236 - 244 (2012/05/04)
The synthesis of azaphilone scaffolds that have been further diversified by cross coupling acylation and amine addition is reported. Methodology development also led to novel modifications including C5 acetoxylation and condensations producing isoquinolin-6(7H) structures. Overall, the library synthesis afforded three azaphilone sublibraries, including vinylogous pyridones which project diversity elements in four sectors of the azaphilone core.
Synthesis and antifungal activity of novel sclerotiorin analogues
Lin, Long,Mulholland, Nick,Wu, Qiong-You,Beattie, David,Huang, Shao-Wei,Irwin, Dianne,Clough, John,Gu, Yu-Cheng,Yang, Guang-Fu
experimental part, p. 4480 - 4491 (2012/09/11)
Sclerotiorin 1, first isolated from Penicillium sclerotiorum, has weak antifungal activity and belongs to the azaphilone-type family of natural products. Several series of sclerotiorin analogues were designed and synthesized with the aim of discovering novel fungicides with improved activity. The syntheses involved two key steps, cycloisomerization and then oxidation, and used a simple and efficient Sonogashira cross-coupling reaction to construct the required functionalized precursor. With sclerotiorin as a control, the activities of the newly synthesized analogues were evaluated against seven fungal pathogens, and several promising candidates (compounds 3a1, 3d2, 3e2, 3f2 and 3k2) with greater activity and simpler structures than sclerotiorin were discovered. In addition, preliminary structure-activity relationships were studied, which revealed that not only the chlorine or bromine substituent at the 5-position of the nucleus but also the phenyl group at the 3-position and the substituent pattern on it contributed crucially to the observed antifungal activity. Analogues with a methyl substituent at the 1-position have reduced levels of activity, while those with a free hydroxyl group in place of acetoxy at the quaternary center of the bicyclic ring system retain activity.
