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Sintesis Dan Uji Molecular Docking Senyawa Hidrazon N’-[(1e)-1-{4-[2-(Morfolin-4-Il)Etoksi] Fenil}Etiliden]Piridin-4-Karbohidrazid Sebagai Agen Anti Kanker Payudara
Hydrazone is a substitution compound with a stable imine-type that possesses an azomethine group (-NH-N=C-R-). Hydrazone is one of the chemical compounds that has garnered attention for development. The purpose of this research is to synthesize the hydrazone compound N’-[(1E)-1-{4-[2-(morpholin-4-yl)ethoxy] phenyl}ethylidene]pyridin-4-carbohydrazide, which has been successfully synthesized through several reaction stages. The first stage involves the formation of o-alkylation of 1-[4-(2-morpholin-4-ethoxy)phenyl]acetophenone by combining 4-hydroxyacetophenone and 4-(2-chloroethyl)morpholine hydrochloride using reflux method and catalyzed with potassium carbonate. The o-alkylation of 1-[4-(2-morpholin-4-ethoxy)phenyl]acetophenone is synthesized using the condensation reaction, yielding a yield of 98,7%. In the next stage, o- alkylation of 1-[4-(2-morpholin-4-ethoxy)phenyl]acetophenone is reacted with isoniazid, producing the target compound using glacial acetic acid catalyst. The synthesis process of the target compound is carried out with microwave irradiation, yielding a yield of 88,6%. The purification of the hydrazone compound is carried out through recrystallization. Its purity is evaluated using TLC, determination of melting point, and HPLC analysis. Furthermore, structural confirmation is based on spectroscopic data from UV, FTIR, 1H-NMR, and LCMS. Molecular docking research on N’-[(1E)-1-{4-[2-(morfolin-4-il)etoksi] fenil}etiliden]piridin-4-karbohidrazid (HDZ-MRF) with estrogen α receptor revealed that the binding free energy (∆Gbind) is -7.9 kcal/mol, indicating that the HDZ-MRF compound has limited biological activity as a breast cancer drug.
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