"Drug Design" et synthèse de nouveaux calix[8]arènes sulfoniques flexibles à activités anticorrosive et anticoagulante

Abstract

"In this work, We developed a new method of the synthesis of sulfonic calix[8]arenes derivatives. We realized four substitution reactions of eight hydroxyl groups of 5,11,17,23,29,35,41,47-octa-tert-butyl-49,50,51,52,53,54,55,56-octakis calix[8]arene and 49,50,51,52,53,54,55,56-octakis-calix[8]arene by 1,3-trimethylene and 1,4- tetramethylene groups, leading respectively to the following four new sulfonic calix[8]arenes : • 5,11,17,23,29,35,41,47-octa-tert-butyl-49,50,51,52,53,54,55,56-octakis- (3-propylsulphonic acid) calix[8]arene. • 49,50,51,52,53,54,55,56-octakis-(3-propylsulphonic acid) calix[8]arene. • 5,11,17,23,29,35,41,47-octa-tert-butyl-49,50,51,52,53,54,55,56-octakis- (4-butylsulphonic acid) calix[8]arene. • 49,50,51,52,53,54,55,56-octakis-(4-butylsulphonic acid) calix[8]arene). The anticorrosive activity of the synthesized calix[8]arenes was studied by the use of the three classical methods (gravimetric, potentiodynamic and impedance). They showed an excellent inhibition of steel corrosion in HCl 1M. The increase of the temperature decreases the inhibitory efficiency and the calixarenes were adsorbed to the surface of steel according to isotherm model of Langmuir, via a chemical adsorption. The synthesized calixarenes showed an excellent in vivo and in vitro anticoagulant activity, especially the derivative 5,11,17,23,29,35,41,47-octa-tertbutyl- 49,50,51,52,53,54,55,56-octakis-(4-butylsulphonic acid) calix[8]arene. The POM (Petra, Osiris, Molinspiration) theory application on the synthesized calixarenes showed that they are not toxic and that they are efficient as well as the clinical coagulation inhibitors."