Abstract
Background: Hydrazonoyl chloride, accessible from the respective 5-amino-8-fluoro-4-oxoquinoline-3-carboxylate, undergoes a reaction with sec-cyclic amines to generate N1-(1-ethyl-8-fluoro-4-oxoquinolin-5-yl)amidrazone carboxylates.
Introduction: A novel set of N1-(1-ethyl-8-fluoro-4-oxoquinolin-5-yl)amidrazone carboxylates (7a-h) incorporating N-piperazines or related congeners was synthesized via interaction of the hy-drazonoyl chloride (6), accessible from the respective 5-amino-8-fluoro-4-oxoquinoline-3-carbox-ylate, with the appropriate sec-cyclic amine. These new compounds were characterized by 1H-NMR, 13C-NMR, and HRMS spectral data and screened for their anticancer activities.
Aims: This study aimed at the synthesis of novel N1-( 4-oxoquinolin-5-yl)amidrazone carboxylate derivatives and investigated their potential as anticancer agents.
Objective: The reaction of hydrazonoyl chloride with the appropriate sec-cyclic amine was applied to synthesize a novel set of N1-(1-ethyl-8-fluoro-4-oxoquinolin-5- yl)amidrazone carboxylates that incorporate N piperazines.
Methods: A direct reaction of piperazines and related sec-cyclic amines with N-(4-oxoquinolin-5-yl)nitrile imine (1,3-dipole) was carried out for 8-10 h.
Results: The 1,3-dipole, generated in situ from its hydrazonoyl chloride precursor in the presence of trimethylamine, is suitable for the facile synthesis of N1-(1-ethyl-8-fluoro-4-oxoquinolin-5-yl)amidrazone carboxylates.
Conclusion: This study led to the successful synthesis of novel N1-(8-fluoro-4-oxoquinolin-5-yl)amidrazones. All the examined compounds showed moderate activity with reasonable IC50 values in the micromolar range compared to Doxorubicin.
Call for Papers in Thematic Issues
Exploring the Role of Chemical Graph Theory in Advancing Current Organic Synthesis
Organic synthesis is a fundamental discipline in chemistry, crucial for the creation of complex molecules with diverse applications in pharmaceuticals, materials science, and beyond. However, the process of designing efficient synthetic routes for target molecules remains challenging. Chemical graph theory, a branch of theoretical chemistry, offers powerful tools for understanding ...read more
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