The synthesis and properties of a calixarene-based ‘sugar bowl’

Linnane, Patrick; James, Tony D.; Shinkai, Seiji

doi:10.1039/c39950001997

Cited by 32 publications

(39 citation statements)

References 10 publications

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“…Of the three possible isomers, the cone-conformer was selectively synthesized. Functionalization proceeded smoothly, using similar examples from the literature (10)(11)(12). The synthetic route is outlined in Scheme I.…”

Section: Resultsmentioning

confidence: 99%

“…This inviting bowl-like shape and their synthetic availability have made calixarenes attractive scaffolds for molecular recognition. Indeed, recent reviews of calixarene chemistry have been largely dedicated toward applications in supramolecular chemistry (10)(11)(12). Of note are calix [4]arene systems designed by van Loon et al (13) and Kok et al (14) to similarly assemble by hydrogen bonding.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and assembly of self-complementary calix[4]arenes.

Shimizu

Rebek

1995

Proc. Natl. Acad. Sci. U.S.A.

283

138

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A calix [4]arene was designed to reversibly dimerize and form an egg-shaped enclosure. Adhesive interactions in the assembly were provided by four self-associating ureas, which form a cyclic array containing 16 hydrogen bonds. The synthesis was completed in four steps from theEvidence for dimerization of the calixarene tetraurea was provided by 'H NMR, mass spectrometry, and the observation of encapsulated molecules. The resulting cavity was of sufficient size to capture guests such as ethyl benzene andp-xylene.

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Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

Synthesis and assembly of self-complementary calix[4]arenes.

Shimizu

Rebek

1995

Proc. Natl. Acad. Sci. U.S.A.

283

138

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“…For example, N-bromosuccinimide has been used for tetrabromination of the tetramethyl ether of calix [4]arene in high yield, [50] while Br 2 has been used for B,D-dibromination of the A,C-dialkyl ether. [51] Similarly, Friedel-Crafts and other electrophilic aromatic substitution conditions were applied to introduce alkyls, NO 2 , SO 3 H, SO 2 Cl, CHO, COR, COAr, CH 2 Cl, ArN 2 , etc. on the upper rim of calixarenes.…”

Section: Calix[4]arene-an Overviewmentioning

confidence: 99%

Functionalized calix[4]arenes as potential therapeutic agents

2017

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Calixarenes, composed of phenolic units linked by methylene bridges at the 2,6-positions, represent a versatile class of macrocyclic compounds in supramolecular chemistry that can host small molecules or ions in their well-defined hydrophobic cavities. In recent years, it has been recognized that this class of compounds has the potential to serve as platform for the design of biological active compounds. Therefore, the calixarenes functionalized with different pharmacophoric groups have been synthesized as target structure by many researchers and were further evaluated for their biological activities. Owing to their promising biological activities such as antiviral, antibacterial, antifungal, and anticancer, the functionalized calixarenes are recently receiving increased attention from pharmaceutical/medicinal chemistry community. In this review, we summarize and discuss the synthetic approaches and the biological potential of functionalized calixarenes, mainly focusing on the selected recent studies for a comprehensive and target-oriented information, which could help in the design and synthesis of new therapeutic agents leading to the development of clinically viable drugs based on these macrocyles. K E Y W O R D Sbiological activity, calixarenes, cone conformation, functionalization, upper/lower rim/annulus

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“…The title compound was prepared starting from the precursor compound 5, 17-dibromo-25,26,27,28-tetrapropoxy-calix[4]arene, which was obtained according to [1], in a similar one-step procedure as described in [2] and recrystallized from chloroform/methanol. In the asymmetric unit, there are two conformational forms which are caused by the disorder of the substituted groups on the lower rims.…”

Section: Source Of Materialsmentioning

confidence: 99%

Crystal structure of 5,17-bis(N-tert-butylhydroxyamine)-25,26,27,28- tetrapropoxycalix[4]arene, C48H66N2O6

Yang

Liu

et al. 2006

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialThe title compound was prepared starting from the precursor compound 5, 17-dibromo-25,26,27,28-tetrapropoxy-calix[4]arene, which was obtained according to [1], in a similar one-step procedure as described in [2] and recrystallized from chloroform/methanol. In the asymmetric unit, there are two conformational forms which are caused by the disorder of the substituted groups on the lower rims. The cone conformation of the calix[4]arene cavity is retained from the precursor, but pinched due to the two OH···N hydrogen bonds between the two N-tert-butyl-hydroxyamine groups on the upper rims. In the first form, the hydrogen bond lengths are 2.06 Å for H5A···N2 and 2.05 Å for H6A···N1, and the angles are 150.0°for O5H5A···N2 and 150.2°for O6H6A···N1. Experimental detailsIn the second form, the hydrogen bond lengths are 2.05 Å for H5A¢···N2 and 2.03 Å for H6A¢···N1, and the angles are 147.8°f or O5¢H5A¢···N2 and 151.4°for O6¢H6A¢···N1. The four dihedral angles are 34.9°for the phenyl ring C9-C14, 38.2°for the phenyl ring C23-C28, 75.1°for the phenyl ring C16-C21, and 76.8°for the phenyl ring C2-C7 to the reference plane defined by the bridging C atoms (here C1, C8, C15 and C22). The distances from C1, C8, C15 and C22 to the reference plane are 0.057 Å, 0.057 Å, 0.056 Å and 0.057 Å, respectively.

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The synthesis and properties of a calixarene-based ‘sugar bowl’

Cited by 32 publications

References 10 publications

Synthesis and assembly of self-complementary calix[4]arenes.

Synthesis and assembly of self-complementary calix[4]arenes.

Functionalized calix[4]arenes as potential therapeutic agents

Crystal structure of 5,17-bis(N-tert-butylhydroxyamine)-25,26,27,28- tetrapropoxycalix[4]arene, C48H66N2O6

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