A SAR study on a series of synthetic lipophilic chalcones as Inhibitor of transcription factor NF-κB

Synthesis and anticancer activity of chalcones derived from vanillin and isovanillin

“…Protection of -OH group of ring B as aryloxy acetic acid (7a) or methoxy (8a) resulted in decreased activity of chalcones 7a and 8a. This is in accordance with the literature report wherein the presence of hydroxyl group in para position of ring B is reported to be essential for activity (Venkateswararao et al, 2012). Variation in substituents in ring A did not lead to results corroborative with the literature which reports that presence of electron-withdrawing group in ring A decreases cytotoxicity whereas electron-donating group increases cytotoxicity in all the five tested cell lines (Bai et al, 2014).…”

Transfer Hydrogenation of Flavanones and ortho‐Hydroxychalcones to 1,3‐Diarylpropanols Catalyzed by CNN Pincer Ruthenium Complexes

“…[4] While the syntheses of flavan-4ols, [5] dihydrochalcones [6] and 1,3-diarylpropanes [7][8][9] have been widely described in the literature, the preparation of orthohydroxy 1,3-diarylpropanols has not been properly covered yet. Interestingly, compounds containing this motif have shown to display inhibitory properties in the transcription factor NF-kB, [10] anti-cholinesterase, [11] anti-inflammatory activity [12] and P-glycoprotein-inhibitory effects (GP-88) [13] (Figure 1). Among the reported methods for the synthesis of orthohydroxy 1,3-diarylpropanols, the model compound 2-(1hydroxy-3-arylpropyl)phenol entails the C=C reduction of chalcones via hydrogenation under pressure using Pd/C followed by C=O reduction with NaBH 4 , affording the product in low yield.…”

“…Among the reported methods for the synthesis of orthohydroxy 1,3-diarylpropanols, the model compound 2-(1hydroxy-3-arylpropyl)phenol entails the C=C reduction of chalcones via hydrogenation under pressure using Pd/C followed by C=O reduction with NaBH 4 , affording the product in low yield. [10] Katagi and co-workers described the reduction of flavone using NaAlH 2 (OCH 2 CH 2 OCH 3 ) 2 to afford the desired product in 33 % yield, [14] with concomitant formation of a functionalized indane from a rearrangement-side reaction. More recently, Zheng and Hall reported the synthesis of 2-(1hydroxy-3-phenypropyl)phenol in moderate yield via zirconium-catalyzed condensation between 3,5-bis (trifluoromethyl)phenylboronic acid, phenol and 2-phenylpropanal followed by hydrolytic oxidation of the corresponding dioxaborin intermediate with H 2 O 2 .…”

Cytotoxicity Assay of 2,4-Dihydroxide-4’-Methoxychalcone Against Cervical (HeLa) Cancer Cell by MTT Assay

“…As a whole, chalcone structure consists of two aromatic rings (A and B) (Han et al, 2019) with disubstituted of a hydroxyl group in ring A and monosubstituted of methoxy in ring B (Mahapatra et al, 2015) have activities moderate level since that substituted important as active site (Venkateswararao et al, 2012). Moreover, it was also has a double bond opening ring of benzene.…”