Synthesis and Antitumor Evaluation of Innovative Naphthalene-Based Heterocycles against MCF7 Breast Cancer Cells

Fouad, Marwa Mohamed; Ali, Korany A.; Mahmoud, Khaled; Ragab, Eman Ali

doi:10.21608/ejchem.2025.373699.11560

Synthesis and Antitumor Evaluation of Innovative Naphthalene-Based Heterocycles against MCF7 Breast Cancer Cells

Document Type : Original Article

Authors

¹ Basic Science Department, Modern Academy for Engineering &Technology, Cairo, Egypt,

² national research centre

³ Department of Chemistry, Faculty of Science, Cairo University

10.21608/ejchem.2025.373699.11560

Abstract

This study aimed to synthesize novel heterocycles containing a naphthyl moiety with the potential to exhibit anticancer effects. The starting material used was (E)-3-(dimethylamino)-1-(2-naphthyl)prop-2-en-1-one (1). Naphthyl-substituted fused pyrimidine derivatives 4 and 5, also pyrazolo[1,5-a]pyrimidines 7a,b were synthesized by reacting enaminone 1 with 3-amino-1,2,4-triazole (2), 2-aminobenzimidazole (3), and azoaminopyrazole derivatives 6a,b, respectively. Additionally, enaminone 1 and hydrazonyl chlorides 8a-f were reacted to produce 9a-f. Hydrazine was then condensed with the pyrazole-3,4-dicarbonyl derivatives 9a,c to yield pyrazolo[3,4-d]pyridazine derivatives 10a and 10c. In the existence of ammonium acetate and glacial acetic acid, enamine 1 reacted with 1,3-diphenylpropane-1,3-dione (11) to afford 3-benzoyl-6-(2-naphthyl)-2-phenylpyridine (13). The structures of the newly synthesized compounds were confirmed using elemental analysis, IR and NMR spectroscopy and mass spectrometry. The MCF7 breast carcinoma cell line was used to evaluate the cytotoxic properties of the developed chemicals. The results indicated that ingredients 9e, 9f and 13 demonstrated significant bioactivity, with compound 13 showing the most promising antitumor effects on the MCF7 cell line. Adrinamycin (Doxorubicin) was used as a positive control.

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