Synthesis and Antitumor Evaluation of Innovative Naphthalene-Based Heterocycles against MCF7 Breast Cancer Cells | ||||
| Egyptian Journal of Chemistry | ||||
| Volume 68, Issue 6, June 2025, Page 463-475 PDF (647.19 K) | ||||
| Document Type: Original Article | ||||
| DOI: 10.21608/ejchem.2025.373699.11560 | ||||
 View on SCiNiTO | ||||
| Authors | ||||
Marwa Mohamed Fouad   1; Korany A. Ali 2; khaled mahmoud 2; Eman Ali Ragab3
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| 1Basic Science Department, Modern Academy for Engineering &Technology, Cairo, Egypt, | ||||
| 2national research centre | ||||
| 3Department of Chemistry, Faculty of Science, Cairo University | ||||
| 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. | ||||
| Keywords | ||||
| Enaminone; pyrazolopyrimidine; azoaminopyrazole; breast-carcinoma; Chi-Square Tests | ||||
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