Abstract

Walaa Hamada Abd-Allah¹ and Mohamed Fathy Elshafie²

DOI : http://dx.doi.org/10.13005/ojc/340228

Series of 1-(N-phenyl-2-(heteroalicyclic-1-yl)acetamido)cyclohexane-1-carboxamide derivatives (5a-m) and 1-(phenyl(heteroalicyclic-1-ylmethyl)amino)cyclohexane-1-carboxamide (6a-f) were designed and synthesized with biological interest through coupling of 1-(2-chloro-N-phenylacetamido)cyclohexane-1-carboxamide (4) and (phenylamino)cycloakanecarboxamide (2) with different amines. The structures of the target compounds were elucidated via IR, ¹H and ¹³C NMR, MS, and microanalysis. Compounds 5a-m and 6a-f were evaluated for their in-vitro antitumor activity against four different cancer cell lines, MCF-7, HepG2, A549, and Caco-2. Compound 5i exhibited a promising activity against breast cancer cell line (IC₅₀ value = 3.25 μM) compared with doxorubicin (IC₅₀ value = 6.77 μM). Results from apoptosis and cell cycle analysis for compound 5i revealed good antitumor activity against MCF-7 cancer cell line and potent inhibition.

1,1-Disubstituted cyclohexane; Amides; Synthesis; Cytotoxic evaluation; Apoptosis

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