Synthesis and Cytotoxic Evaluation of Alkoxylated Chalcones

Abstract

A series of chalcones a1-20 bearing a 4-OMe groups on the A-ring were initially synthesized and their anticancer activities towards HepG2 cells evaluated. Subsequently, a series of chalcones b1-42 bearing methoxy groups at the 2' and 6'-positions of the B-ring were synthesized and their anticancer activities towards five human cancer cell lines (HepG2, HeLa, MCF-7, A549 and SW1990) and two non-tumoral human cell lines evaluated. The results showed that six compounds (b6, b8, b11, b16, b18, b22, b23 and b29) displayed promising activities, with compounds b22 and b29 in particular showing higher levels of activity than etoposide against all five cancer cell lines. Compound b29 showed a promising SI value compared with both HMLE and L02 (2.1-6.5 fold in HMLE and > 33 > 103.1 fold in L02, respectively).

Synthesis and anticancer activity of chalcones derived from vanillin and isovanillin

“…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). Also there is another report which says introduction of any substituent (either electron donating or electron withdrawing) decreases the cytotoxicity as compared to unsubstituted chalcones on the tested cell lines (Prabhakar et al, 2014).…”

Design, synthesis and biological evaluation of chalcone analogues with novel dual antioxidant mechanisms as potential anti-ischemic stroke agents

“…In other cases, the products were purified by using silica gel chromatography. Compounds 1 – 7 , 9 – 10 , 13 , 14 , 16 , 19 – 20 , 22 , 24 , 26 , 28, 32, 36 , 38 and 40 were published previously in the literature74., 75., 76., 77., 78., 79., 80., 81., 82., 83., 84., 85., 86., 87., 88., 89., and their spectral data are in the Supporting Information. The spectral data of novel or unreported compounds are listed as follows.…”

New Fluoro‐ and Trifluoromethyl‐Substituted Trimethoxychalcones as Anticancer Agents: Synthesis, Bio‐evaluation, and Computational Studies

“…These substituents have been reported to be the source of chalcones' biological activities (Figure 4). [9,12,16,[21][22][23] The aforementioned findings motivate us to design a series of chalcones with trimethoxy (À OMe) groups at positions 2,4,6 of the A ring and F/CF 3 groups at various positions of the B ring (Figure 5). As a result, in continuation of our recent studies on the synthesis of anticancer agents, [15,[24][25][26] we describe here the synthesis of novel fluoro and trifluoromethyl substituted trimethoxychalcones to investigate their anticancer properties.…”

“…[5] In the literature, there are also cytotoxicity studies with various chalcone derivatives and their analogs in many cell lines, as well as data on the effectiveness of these compounds. [7][8][9][10][11][12][13] Many researchers have created methoxy chalcones and investigated their biological properties due to the presence of poly-methoxy groups in the chalcone structures of many naturally occurring anticancer agents. [14] When the findings of the studies are examined, it is discovered that the presence of methoxy groups in these compounds significantly contributes to their cytotoxicity (Figure 2).…”