Synthesis and anti-oxidant activity of (5E,9E)-16-(substituted)-7,8-dihydro-16λ(5) -dibenzo[d,l][1,3,7,10,2]dioxadiazaphosphacyclotridecine-16-ones.

A new class of biologically active 13-membered phosphorus-macroheterocycles (6a-l) were conveniently synthesized from 1,2-bis(salicylidene amino)-phenylene (1), by treating with phosporusoxychloride (3) and followed by reacting with various aromatic thiols and amines (5f-l) in one path, and in another path 1 was directly treated with various phosphorodichloridates (2a-e) in the presence of triethylamine at 0-10°C under N(2) atmosphere in THF. All the title compounds were confirmed by analytical and spectral data (IR, (1) H-, (13) C-, (31) P-NMR, and mass spectra) and screened for anti-oxidant activity. Among these compounds, 6k, 6e, and 6l containing nitro, fluoro, and chloro groups as substituents on the phenyl ring exhibited high anti-oxidant activity with effective inhibitory concentration (IC(50) ) values.