Synthesis and Anti-Oxidant Activity of (5E,9E)-16-(Substituted)-7,8-dihydro-16λ5-dibenzo[d,l][1,3,7,10,2]dioxadiazaphosphacyclotridecine-16-ones

• Published in: Archiv der Pharmazie (Weinheim) 2012-06, Vol.345 (6), p.495-502
• Main Authors: Reddy, Chinta Raveendra, Rani, Chinthaparthi Radha, Sekhar, Kuruva Chandra, Reddy, Gangireddy Chandra Sekhar, Raju, Chamarthi Naga
• Format: Article
• Language: English
• Subjects: Anti-oxidant activity; Phosphorus macrocycles; Radical scavenging activity
• ISSN: 0365-6233; 1521-4184
• DOI: 10.1002/ardp.201100204

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 N2 atmosphere in THF. All the title compounds were confirmed by analytical and spectral data (IR, 1H‐, 13C‐, 31P‐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 (IC50) values. A new class of anti‐oxidatively active 13‐membered phosphorus‐macroheterocycles were conveniently synthesized and their activity was measured by DPPH radical scavenging, reducing power assay, and hydroxyl radical scavenging methods. The title compounds possess significant anti‐oxidant activity.