Design, Synthesis, and Structure–Activity Relationships of Bavachinin Analogues as Peroxisome Proliferator‐Activated Receptor γ Agonists

Abstract

Peroxisome proliferator‐activated receptor γ (PPARγ) agonists have been used for the treatment of diabetes with the effect of lowering blood glucose levels and improving insulin sensitivity. Natural compounds such as flavones, flavanones, and isoflavones have shown excellent PPARγ agonist activity. In this study, analogues of bavachinin were designed, synthesized, and evaluated by reporter gene assays for PPARγ agonist activity. Preliminary structure–activity relationships for these bavachinin analogues have been summarized, and seven compounds were found to have higher PPARγ agonist activities than the parent flavanone bavachinin.

Biological Properties and Absolute Configuration of Flavanones From Calceolariathyrsiflora Graham

“…per OH group) dropwise at 0°C, and the reaction mixture stirred at room temperature until the reaction completed. The 1 H, 13 C-NMR and 2D NMR data were consistent with the reported structures ( Khupse and Erhardt, 2007 ; Du et al., 2017 ; Barbuščáková et al., 2018 ).…”

Induction of G2/M Cell Cycle Arrest via p38/p21Waf1/Cip1-Dependent Signaling Pathway Activation by Bavachinin in Non-Small-Cell Lung Cancer Cells

“…Bavachinin, a prenylflavone in the seed of Psoralea corylifolia , has been indicated as a natural PPARγ agonist. Structurally, the isopentenyl group and the methoxy group of the A ring have critical effects on the PPARγ agonist activity of bavachinin ( Figure 1 A) [ 40 ]. Therefore, bavachinin has been directed against lung cancer cells proliferation, by targeting the PPARγ ROS-regulated signaling pathway [ 16 ].…”

Study on the 2‐Phenylchroman‐4‐One Derivatives and their anti‐MERS‐CoV Activities

“…The synthesis of racemic mixtures of bavachin derivatives were reported and these compounds have been proven to be PPAR agonists and anticancer reagents . However, exchanges of phenol group to aniline group have not been tried.…”

“…The double bond in the side chain of 1a was reduced by hydrogenation with Pd/C to prepare 2a , and oxidation of chromane ring with I 2 was performed to produce 3a (Scheme ). 6a was synthesized by the modified procedure of that of 1a . 4 was reacted with N ‐Boc‐protected 4‐aminobenzaldehyde by aldol condensation to give 5 , which was cyclized by KF to produce 6a (Scheme 3).…”