Synthesis and Modification of Novel Iminecalix[4]arene Derivatives

Abstract

The synthesis of novel iminecalix [4]arenes and further modification thereafter is described using a synthetic strategy. The reaction of the benzaldehyde derivatives with tetraamine functions on the calix[4]arene easily afforded the pure compounds in 92.4-95.7% yields, regardless of the effect of the substituents on the benzaldehyde derivatives. These compounds were stable under the conditions to obtain their analogue dialkylated in the narrow rim, with 83.2-89.9% yields. Characterization of the newly synthesized iminecalix[4]arene derivatives by spectroscopic methods revealed that all compounds are in the cone conformations.

Biological applications of functionalized calixarenes

“…[42][43][44][45] Based on the knowledge of the mixed-self assembled monolayer and the molecular recognition properties of the imincalix [4]arene 5, and aminocalix [4]arnes 6-9, recently, T. Kim et al introduced the phenomenon of molecular recognition to immobilize oligonucleotides on aminocalix [4]arene (AMCA) slides for the production of 9G DNAChips. 46 The preparation of the 9G DNAChip and the hybridization thereafter is briefly explained in Scheme 4.…”

Macrocycles and Supramolecules as Antioxidants: Excellent Scaffolds for Development of Potential Therapeutic Agents

“…The synergism between the calix [4]arene moiety and the para-azo substituent groups at the upper rim contributed significantly towards the antiradical and antioxidant activity. Iminecalix [4]arene derivatives are known to possess a deep cavity and hyperconjugation [53]. The water-soluble iminecalix [4]arene derivatives are reported for the molecular recognition of various organic molecules [54].…”

“…Iminecalix [4]arene derivatives are known to possess a deep cavity and hyperconjugation [53]. The water-soluble iminecalix [4]arene derivatives are reported for the molecular recognition of various organic molecules [54].…”

“…General scheme for the synthesis of resorcinarene derivatives.In 2009, Vovk et al reported on the antioxidant and antiradical activities of resorcinarene tetranitroxides (Figure 8)[67]. They synthesized the resorcinarene(48,49) derivatives(50)(51)(52)(53) by the aminomethylation of resorcinarene octols with 4-amino-TEMPO TEMPO ((4-Amino-2,2,6,6-tetramethylpiperidine-1-oxyl), and studied their antioxidant activities. They found that the Tetra-TEMPO resorcinarenes(50)(51)(52)(53) are efficient scavengers of DPPH radicals and showed superoxide dismutase-like activity.…”

Water-Soluble Calix[4]arene Derivatives: Binding Stoichiometry and Spectroscopic Evaluation of the Host-Guest Recognition Mechanism

“…42,43 The negatively charged four carboxylate functions on the top of the deep hydrophobic cavity play a major role in the recognition of charged molecular species. The 1 H NMR titration experiments revealed that host (16) binds with cationic (15, 21, 22) and neutral guests (17)(18)(19)(20) in water, with high binding constants in order of 10 4 -10 5 M -1 .…”