Synthesis of Some Chalcone Derivatives, in Vitro and in Silico Toxicity Evaluation

Abstract

Chalcone can be synthesized using some methods, but conventional Claisen-Schmidt condensation is still the best method. The objevtives of this study were to synthesize some chalcone derivatives using conventional Claisen-Schmidt condensation by reacting 2-hydroxyacetophenone and some substituted benzaldehydes using NaOH 40%, followed by evaluating their cytotoxicity in vitro against HeLa cancer cells line using MTT method and analyzing molecular docking on p53 and MDM2 interaction. Cytotoxicity test exhibited that 2,5-dimethoxy-2´hydroxychalcone and 4-chloro-2'-hydroxychalcone gave very low IC 50 , but both did not show potential apoptosis activity, while in docking analysis 4-chloro-2'-hydroxychalcone showing the best results.

Stereoselective Synthesis of Flavonoids: A Brief Overview

“…Claisen-Schmidt reaction [21,30,31] Friedel-Crafts reaction [21] Heck coupling [32] Suzuki-Miyaura reaction [62] Flavonols Algar-Flynn-Oyamada reaction [21,34] Karl von Auwers reaction [60] Kostanecki methodology [29] Flavanones Intramolecular cyclisation of 2 -hydroxychalcones [36][37][38][39][40][41][42][43] Flavones Oxidative cyclisation of 2 -hydroxychalcones [44][45][46][47][48][49][50][51] Allan-Robinson reaction [21,52] Baker-Venkataraman reaction [21,54] Kostanecki reaction [55] Mentzer pyrone synthesis [57] Suzuki-Miyaura reaction [62] Isoflavones Allan-Robinson reaction [21,52] Suzuki-Miyaura reaction [62] Deoxybenzoin route [22] Reductive cleavage of isoxazoles [23] Intramolecular ketene cycloaddition followed by decarboxylation…”

“…Considering the biological and industrial potential of natural flavonoids, several chemical methodologies have been developed to obtain nature-inspired flavonoids, as summarised in Table 1 [ 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 ].…”

“…Regarding the Claisen–Schmidt reaction, it comprises the reaction of an aromatic aldehyde and a substituted acetophenone under basic catalysis (Scheme A, Figure 2 ). This process can be improved with recourse to microwave and ultrasound [ 30 , 33 ], resulting in the enhancement of the yields and a reduction in the reaction time [ 31 ]. With respect to the Friedel–Crafts method, 2′-hydroxychalcones are originated from the condensation of ( E )-3-phenylprop-2-enoyl chloride and phenols through AlCl 3 catalysis [ 21 ] (Scheme B, Figure 2 ).…”

“…Molecules 2023, 28, x FOR PEER REVIEW 3 of 34 [30,33], resulting in the enhancement of the yields and a reduction in the reaction time [31]. With respect to the Friedel-Crafts method, 2′-hydroxychalcones are originated from the condensation of (E)-3-phenylprop-2-enoyl chloride and phenols through AlCl3 catalysis [21] (Scheme B, Figure 2).…”

An Experimental and Computational Approach to The Microwave‐Assisted Synthesis of 2’‐Hydoxychalcone Derivatives in 1‐Dodecyl‐3‐Methylimidazolium Bromide ([DDMIm]Br) Ionic Liquids

“…Various schemes are available for synthesizing different chalcone analogs, making them a versatile class of compounds with promising prospects in medicine. [6,7] Chalcone derivatives are typically synthesized through Claisen-Schmidt condensation reactions using benzaldehyde and acetophenone derivatives under basic conditions. [8] However, these reactions often require large amounts of volatile organic solvents, which contribute to environmental pollution.…”