Synthesis and Characterization of Macrocyclic Chiral Tröger's Base Phenhomazine Candidates as Anticancer Agent.

1,4,7,10-Tetraoxa10trögerophane was synthesized from its corresponding precursors. Heating of with p-nitrophenoxide afforded bis(p-nitrophenyl)ether , which was treated with hydrazine hydrate to give bis(p-aminophenyl)ether . Treatment of with paraformaldehyde and triflouroacetic anhydride gave trögerophane . Reaction of with trifluroacetic anhydride afforded phenhomazine derivative , which was treated with potassium carbonate to afford tetrahydrophenhomazine . Finally, reaction of with phenacylchloride, bromoacetic acid, or ethyl bromoacetate in the presence of triethyl amine under reflux, afforded the corresponding macrocyclic compounds and , respectively. The synthesized trögerophane,precursors and its newly synthesized phenhomazines derivatives were screened for anticancer activity. Results revealed that 1,4,7,10-tetraoxa10trögerophane had a promising selectivity towards colon cancer cell line with an IC of 92.7 µg/ml.