Novel acyclic ligands for metal cations based on the adjacent bistetrahydrofuran as analogs of natural Annonaceous acetogenins

Abstract

The acyclic ligands with an adjacent bistetrahydrofuran (THF) skeleton have been synthesized as analogs of bullatacin, a representative natural product in a family of Annonaceous acetogenins, and their binding properties toward metal cations have been investigated. The dihydroxyl bis-THF ligands with alkyl chains showed specific binding toward Ca 2+, and those with acetamido groups exhibited potent binding with Ca 2+ and Mg 2+. The ligand with ether chains showed higher affinity toward Mg 2+. These binding properties which depend on the nature of side chains and their stereochemistry have been analyzed by molecular modeling.