Synthesis and Properties ofO‐Glycosyl Calix[4]Arenes (Calixsugars)

Abstract

Model 0-glycosylation reactions at either rim of calix [4]

Extended Structures Built on a Triphenoxymethane Platform −C3-Symmetric, Conformational Mimics of Calix[n]arenes

“…[1Ϫ4] These macrocycles maintain reactive hydroxyl groups about their rims, and with the appropriate pendant arms, macrocycles with diverse properties can be produced. Chemical modifications with esters, [5] glycols, [3] sugars, [6] Schiff bases, [7] and peptides [8] produce compounds capable of binding a range of substrates from alkali [9] and lanthanide metals [9] to proteins. [10] Unfortunately, calixarene-like macrocycles with only three oxygen donors are often difficult to prepare.…”

“…Moreover, the systematic substitution of only three of the phenolic oxygens is quite troublesome for most of the calix[n]arenes. Trisubstituted macrocycles can be isolated through the selective functionalization of calix [6]arene, [14Ϫ17] but, as before, the larger backbone of this compound engenders the macrocycle with immense flexibility, [18] complicating the solution structure of the larger constructs. Conformationally rigid molecules with three oxygen donor arms have been developed from scyllo-inositol and cis,cis-cyclododecane- 1,5,9-triol, but these molecules are quite difficult to prepare, requiring the three phenolate arms point up with respect to the central methine.…”

Curcumin: a calixarene derivative micelle potentiates anti-breast cancer stem cells effects in xenografted, triple-negative breast cancer mouse models

“…POCA4C6 was synthesized as described (Mo et al, 2015), in which the lowest-yield step of formulation (70% yield) was adapted from Dondoni et al (1997). Briefly, n-hexyl groups were added to calix [4]arene in DMF using bromohexane and sodium hydride, formulation was carried out via the Duff reactio, and the formulated product was reduced to the corresponding alcohol using sodium borohydride.…”

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

“…A number of calixsugars have been developed 49 and their binding characteristics studied. Neutral guests such as carbohydrates and N-protected www.intechopen.com amino acids failed to bind.…”