SYNTHESIS AND BIOLOGICAL EVALUATION OF COPPER COMPLEXES WITH ORGANIC LIGANDS BASED ON (E)-3-(4-(DIMETHYLAMINO)PHENYL)-1-(PYRIDIN-2-YL)PROP-2-EN-1-ONE
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Date
2023-05-28
Authors
Qais Awad Mohammad Wawi
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Abstract
Background: Chalcone is an organic compound found in a variety of plants and fruits; it is classified as a phytochemical, specifically a polyphenol. Chalcone is important in the synthesis of many compounds, especially polyphenol derivatives. In addition, it has great medical importance as it is used as an antibiotic to treat cancer. What distinguishes it is that it is non-toxic or has very little toxicity towards normal cells, depending on the source of synthesis. Organic compounds and chalcones, in particular, with metals form complexes with greater activity from their origin; these properties can be used in many fields.
Objectives: The thesis aims to synthesize new organic compounds and their copper complexes formed based on (E)-3-(4-(dimethylamino)phenyl)-1-(pyridin-2-yl)prop-2-en-1-one (102), then evaluate them biologically.
Methodology: Under basic conditions, the condensation reaction was used to prepare compounds. Chalcone (102) was prepared and then reacted with compounds (106, 108, 110, 112 and Dichloromethane) to prepare organic compounds (105, 107, 109, 111, and 118). It then reacted with a solution of copper (II) to prepare the copper complexes. The reactions were monitored using TLC. The prepared compounds were purified and then characterized using NMR, IR, and UV/VIS spectroscopies. In the end, their toxic activity was examined on MEF-1 and B16F10 cells.
Results: The results show that most of the compounds possess pigment properties. Chalcone (102) and its complexes were found to be more bioactive. While the other compounds were toxic to normal cells.
Conclusion:
• Chalcone (102) and compound (105) are produced in basic conditions, but (107, 109, and 111) require acidic conditions.
• The interaction of dichloromethane with chalcone (102) has been confirmed.
• All organic compounds that are synthesized have a conjugated chemical system that enables them to bind and interact with copper II, normal cells, and cancer cells.
• The best anticancer is chalcone (102) and its copper complex (113).
• The activity of copper complexes is greater than that of their constituent organic ligands.
• This research advances our understanding of the reaction conditions required for the synthesis of the aforementioned compounds.
Keywords: Chalcone, Chemical synthesis, Organometallic Complexes’, Copper (II) complexes, Cancer, Anticancer.