Synthesis of Chalcone Derivatives and Their <i>in vitro</i> Anticancer Test Against Breast (T47D) and Colon (WiDr) Cancer Cell Line

Abstract

The synthesis of chalcone derivatives as target compounds and anticancer test against breast (T47D) and colon (WiDr) cell line had been performed. The synthesis was performed by Claisen-Schmidt condensation by using acetophenone and benzaldehyde derivatives. The anticancer activity test of chalcone derivatives was carried out by MTT assay against T47D and WiDr cell lines. The synthesis was started by reacting 4-hydroxyacetophenone and benzaldehyde derivatives such as p-anisaldehyde (chalcone A [(E)-4'-hydroxy-4-methoxychalcone]), veratraldehyde (chalcone B [(E)-4'-hydroxy-3,4-dimethoxychalcone]), 4-chlorobenzaldehyde (chalcone C [(E)-4'-hydroxy-4-chlorochalcone]) and 2,4-dihydroxyacetophenone with 4-chlorobenzaldehyde (chalcone D [(E)-2',4'-dihydroxy-4-chlorochalcone]) in methanol as solvent. The synthesis was carried out in alkaline condition (KOH) by stirring the mixture at room temperature for 48 h. The structures of products were identified by FTIR, GC-MS, 1H- and 13C-NMR spectrometers. The results showed that the chalcone derivatives (A-D) were yielded in 96; 97; 96; and 93%, respectively as yellow solid. The anticancer test indicated that the chalcone D was the most active towards T47D cell line with IC50 of 42.66 μg/mL and the chalcone C was the most active against WiDr cell line with IC50 of 20.42 μg/mL.

Design, Synthesis, and Evaluation of Some Novel Heterocycles Bearing Pyrazole Moiety as Potential Anticancer Agents

“…As a continuation of our efforts in respect of synthesizing biologically active heterocyclic compounds especially those with anticipated cytotoxic activity , we aimed to synthesize new series of pyran, chromone, and pyridine derivatives bearing pyrazole moiety in the hope that new anticancer agents might be detected. The substituted chalconated pyrazole derivative 1 was synthesized by Claisen–Schmidt condensation reaction . Thus, the reaction of o ‐hydroxyacetophenone with 1,3‐diphenylpyrazole‐4‐carboxylaldehyde in methanolic potassium hydroxide at room temperature for 12 h furnished ( E )‐3‐(1,3‐diphenyl‐1 H ‐pyrazol‐4‐yl)‐1‐(2‐hydroxyphenyl)prop‐2‐en‐1‐one 1 (Scheme ).…”

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

“…Hence we assumed that activity in vitro of chalcone against a panel of human cervical cell lines (HeLa) by applying 3-(4,5-dimethylthiazol-2-yl)2,5-diphenyl tetrazolium bromide (MTT) assay as the most popular assessment of viability and cytotoxicity (Pascua-Maestro et al, 2018). Chalcone has an active compound as inhibition of cell growth with IC50 value less than 20 g/mL, moderate active with IC50 value 20-100 g /mL and not active in the inhibition of cell growth if IC50 value than 100 g /mL (Anwar et al, 2018). Based on IC50 references, chalcone synthesized has moderate activity with IC50 (percentage at which 50% of HeLa cells are dead) value shown in Table 1, but that activity of the compound is not selective because of that activity against normal cell (Vero) by 42,29 g /mL with the low selectivity index 0,57.…”

“…Cancer is a disease caused by abnormal and uncontrolled cell growth (Anwar et al, 2018). In its development, cancer cells can spread to other parts of the body and end in death.…”

Synthesis of Chalcones Derivatives and Their Biological Activities: A Review

“…Treatment of hydroxyacetophenone 51 with benzaldehyde derivative 52 in 50% KOH provided the corresponding chalcones 53 – 56 , and the highest yield of chalcones ranged from 93 to 97%. 41 On the other hand, chalcone 53 was prepared in a low 32% yield in the presence of KOH as the catalyst, 42 whereas chalcone B was synthesized with BF 3 -Et 2 O catalyst in a high yield 90%. 43 Reaction of veratraldehyde with 4-hydroxyacetophenone yielded chalcone 54 in a high 97% yield.…”