Syntheses and properties of dithia-tetrahomodiaza-calix[4]arenes bridged by cystine unit

✍ Scribed by Kazuaki Ito; Akane Suzuki; Naoto Ito; Hiroyuki Teraura; Yoshihiro Ohba

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2003
• Tongue: English
• Weight: 113 KB
• Volume: 40
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570400302

✦ Synopsis

Abstract

Dithia‐tetrahomodiaza‐calix[4]arenes were synthesized by the cyclization reactions of bis(3‐(chloro‐methyl)‐2‐hydroxyphenyl)sulfide with cystine peptides in moderate yields. Conformational analysis of the macrocycles by using nmr spectroscopy reveled that the cyclophanes adopt a cone‐like form as a preferable conformation and the cystine bridge moiety is incorporated in the cavity. The calixarene analogs can extract transion metals such as Zn^2+^ and Cu^2+^ ions from an aqueous phase into chloroform.