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

Shigeki Sasaki, Katsunori Maruta, Hiroyuki Naito, Rie Maemura, Eiji Kawahara, Minoru Maeda

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

The acrylic 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 towards 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+ and Mg2+. The ligand with ether chains showed higher affinity toward Mg2+. These binding properties which depend on the nature of side chains and their stereochemistry have been analyzed by molecular modeling.

Original languageEnglish
Pages (from-to)2401-2410
Number of pages10
JournalTetrahedron
Volume54
Issue number11
DOIs
Publication statusPublished - Mar 12 1998

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Acetogenins
Cations
Metals
Ligands
Stereochemistry
Molecular modeling
Biological Products
Skeleton
Ether
Acrylics

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Novel acyclic ligands for metal cations based on the adjacent bistetrahydrofuran as analogs of natural Annonaceous acetogenins. / Sasaki, Shigeki; Maruta, Katsunori; Naito, Hiroyuki; Maemura, Rie; Kawahara, Eiji; Maeda, Minoru.

In: Tetrahedron, Vol. 54, No. 11, 12.03.1998, p. 2401-2410.

Research output: Contribution to journalArticle

Sasaki, Shigeki ; Maruta, Katsunori ; Naito, Hiroyuki ; Maemura, Rie ; Kawahara, Eiji ; Maeda, Minoru. / Novel acyclic ligands for metal cations based on the adjacent bistetrahydrofuran as analogs of natural Annonaceous acetogenins. In: Tetrahedron. 1998 ; Vol. 54, No. 11. pp. 2401-2410.
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