Synthesis of Flavone Derivatives via N-Amination and Evaluation of Their Anticancer Activities

Abstract

Seventeen new flavone derivatives substituted at the 4′-OH position were designed, synthesized and evaluated for their anticancer and antibacterial activities. Among them, compounds 3, 4, 6f, 6e, 6b, 6c and 6k demonstrated the most potent antiproliferative activities against a human erythroleukemia cell line (HEL) and a prostate cancer cell line (PC3). The results also showed that the IC50 value of compounds 3, 4, 6f, 6e, 6b, 6c and 6k were close to that of the anticancer drug cisplatin (DDP) and lower than that of apigenin. All of the derivatives did not present antibacterial activities. The structure–activity relationships evaluation showed that the configuration of methyl amino acid might affect their biological activities.

A novel bactericidal small molecule, STK-35, and its derivative, STK-66, as antibacterial agents against Gram-negative pathogenic bacteria in vitro and in vivo

“…Thus, we speculated that both of the core nucleus and the groups on the core nucleus might be responsible for the antibacterial activity of STK-35/66, including the -NO 2 , -OOH and N-cyclopropyl groups. Similarly, these active groups have been previously reported as effective antibacterial active group (Zitko et al 2018;Zhang et al 2019b;Asiri et al 2021). In the present study, STK-35 and STK-66 showed the most effective antimicrobial activity against type strains and MDR clinical isolates of Gram-negative pathogens (A. baumannii, E. coli, K. pneumoniae and P. aeruginosa), with minimal inhibitory concentrations (MICs) ranging from 0Á0625 to 8 μg ml −1 and minimal bactericidal concentrations (MBCs) from 0Á125 to 16 μg ml −1 (Table 1 and Table S1).…”

Flavones and Related Compounds: Synthesis and Biological Activity

“…At present, the cyclization of o -hydroxychalcones using iodine in dimethyl sulfoxide still represents the principal method for the synthesis of flavones and their analogs with various structures. This method is still finding multiple applications because it generally allows for obtaining the target compounds with high yields, while the o -hydroxychalcones needed as precursors can be easily obtained via Claisen–Schmidt condensation [ 30 , 34 , 35 , 46 , 47 , 61 ].…”

Recent advances in the synthesis of 4H-chromen-4-ones (2012 − 2021)

“…A wide range of 2-aryl-4H-chromen-4-ones, commonly known as flavones, was synthesized via cyclodehydrogenation reaction of (E)-2 0 -hydroxychalcones in the presence of a catalytic amount of molecular iodine in DMSO. The reaction proceeds in a short period of time (15 min to 8 h) and temperatures ranging from 100 °C, 61,62 110 °C, 63,64 120 °C, 65 130 °C, 66,67 140 °C, 68-70 160 °C, 71,72 °C73 to reflux conditions. [74][75][76][77][78][79][80][81][82][83][84][85] The mechanism involves addition of iodine to the CαdCβ double bond; elimination of HI to form the α-iodinated chalcone; cyclization to chroman-4-one via attack of the hydroxyl group to the C-β position and finally elimination of a second HI to afford the desired 4H-chromen-4-one.…”