Synthesis of some new macrocyclic diamides based on dibenzosulfide as N-pivot lariat ethers

Abstract

Background: 18-memberd ring of tri-aza dibenzo sulfide (TTD) and dibenzo sulfoxide (TSD) macrocyclic diamides showed the oxidative radical forming ability and further strengthened the documentation of their cytotoxicity effects through lipids, proteins and DNA oxidation damages. With this in mind, our group synthesized some novel macrocyclic base on TTD diamides and a podand Methods: Novel aza macrocyclic diamides were synthesized based on dibenzosulfide using of diester method as N-pivot Lariat ethers from the michael reaction and nucleophilic attack to epoxide ring as a key strategy of corresponding Diamide with acrylonitrile, epoxy-styrene and 1, 2-epoxypropane at reflux in dichloromethane in good overall yields. In addition, a podand was synthesized based on dibenzosulfoxide with epichlorohydrin at reflux in methanol. Results: The structures of these compounds were confirmed using IR,1H NMR and13C NMR spectroscopy. Conclusion: The presence of additional oxygen atom considerably increases its hydrogen binding capacity and this property can improve biological and complexation characteristics of primary 18-Membered-ring tri-aza Macrocyclic diamide (TTD). Copyright © 2013 by Tabriz University of Medical Sciences.