NOVEL ACYCLIC LIGANDS FOR METAL-CATIONS BASED ON THE ADJACENT BISTETRAHYDROFURAN AS ANALOGS OF NATURAL ANNONACEOUS ACETOGENINS

The acyclic ligands with an adjacent bistetrahydrofuran (THF) skeleton have been synthesized as analogs of bullatacin, a representative natu ral 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 Ca2, and those with acetamido groups exhibited potent binding with Ca2+ a nd Mg2+. 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. ( C) 1998 Elsevier Science Ltd. All rights reserved.