SYNTHESIS A NEW SERIES OF UNSYMMETRICAL MACRO CYCLIC SCHIFF BASES BY [1+1] CYCL-OADDITION REACTION
DOI:
https://doi.org/10.56286/gr40e283Keywords:
Macrocyclic Schiff bases, Anticancer activity, 1,4-dihydropyridine, Hydrazide, Breast cancerAbstract
This study involves the synthesis of macrocyclic schiff bases also their structural properties and biological activity. Started by preparation two starting materials DHP derivatives due to hantzsch reaction (R1 and R3), then reacting 3,5-diacetyl-2,6-dimethyl-1,4-dihyropyridine DHP(R1) with diamine derivatives including benzidine, 1,3diamino propane 1,2-diamino cyclohexane and ethylene diamine lead to synthesis macrocyclic Schiff bases (R4-R7). In contrast macrocyclic Schiff bases (R8-R9) prepared through the reacting 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarbohydrazide (R3) with acetyl acetone and 3,5-diacetyl-2,6-dimethyl-1,4-dihyropyridine, respectively. All condensation reactions were conducted under conventional reflux conditions. The structures of the synthesized compounds were characterized using carbon-13 nuclear magnetic resonance (¹³C NMR), proton nuclear magnetic resonance (¹H NMR), and Fourier-transform infrared (FTIR) spectroscopy, as well as their physical properties such as melting point, TLC chromatography, color and yield. The spectroscopic data confirmed the successful formation of the proposed macrocyclic Schiff base structures, demonstrating the efficiency of the synthetic methodology and the high purity of the obtained products. The biological activity of compound R8 was evaluated against MCF-7 breast cancer cell lines using the MTT assay.
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