Abstract
1,4,7,10-Tetraoxa[10](2,8)trögerophane
5
was synthesized from its corresponding precursors. Heating of
2
with p-nitrophenoxide afforded bis(p-nitrophenyl)ether
3
, which was treated with hydrazine hydrate to give bis(p-aminophenyl)ether
4
. Treatment of
4
with paraformaldehyde and triflouroacetic anhydride gave trögerophane
5
. Reaction of
5
with trifluroacetic anhydride afforded phenhomazine derivative
6
, which was treated with potassium carbonate to afford tetrahydrophenhomazine
7
. Finally, reaction of
7
with phenacylchloride, bromoacetic acid, or ethyl bromoacetate in the presence of triethyl amine under reflux, afforded the corresponding macrocyclic compounds
8, 9
and
10
, respectively. The synthesized trögerophane,precursors and its newly synthesized phenhomazines derivatives were screened for anticancer activity. Results revealed that 1,4,7,10-tetraoxa[10](2,8)trögerophane had a promising selectivity towards colon cancer cell line with an IC
50
of 92.7 µg/ml.