Synthesis of Bridged Thiourea Calix-sugar

Saitz-Barria, Claudio; Torres‐Pinedo, Antonio; Santoyo‐González, Francisco

doi:10.1055/s-1999-3175

Cited by 24 publications

(8 citation statements)

References 29 publications

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“…As example, 2-thio-a-sialosides have been efficiently conjugated to a calix [4]arene scaffold via nucleophilic substitution, providing extended and water-soluble clusters 109 that may exhibit up to 16 dense clustered epitopes. 110 Wittig olefination, 111,112 Pd-catalyzed Sonogashira cross coupling, 113 click chemistry, 114,115 and azide-nitrile cycloaddition 116 [118][119][120][121] (which can act as hydrogen-bonding groups) have been described and have afforded elongated nanostructures with tailored spacer arms. These have shown promising applications as drug delivery systems via host-guest supramolecular chemistry.…”

Section: Glycoclusters From Branched Aromatic Scaffoldsmentioning

confidence: 99%

“…110 Wittig olefination, 111,112 Pd-catalyzed Sonogashira cross coupling, 113 click chemistry, 114,115 and azide-nitrile cycloaddition 116 diversified calyx sugars. In addition, efficient introduction of biologically relevant carbohydrates on calix[n]arenes, through amide 117 or thiourea linkages [118][119][120][121] (which can act as hydrogen-bonding groups) have been described and have afforded elongated nanostructures with tailored spacer arms. These have shown promising applications as drug delivery systems via host-guest supramolecular chemistry.…”

Section: Glycoclusters From Branched Aromatic Scaffoldsmentioning

confidence: 99%

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Design and Creativity in Synthesis of Multivalent Neoglycoconjugates

Chabre

Roy

2010

Advances in Carbohydrate Chemistry and Biochemistry

309

208

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From the authors' opinion, this chapter constitutes a modest extension of the seminal and inspiring contribution of Stowell and Lee on neoglycoconjugates published in this series [C. P. Stowell and Y. C. Lee, Adv. Carbohydr. Chem. Biochem., 37 (1980) 225-281]. The outstanding progresses achieved since then in the field of the "glycoside cluster effect" has witnessed considerable creativity in the design and synthetic strategies toward a vast array of novel carbohydrate structures and reflects the dynamic activity in the field even since the recent chapter by the Nicotra group in this series [F. Nicotra, L. Cipolla, F. Peri, B. La Ferla, and C. Radaelli, Adv. Carbohydr. Chem. Biochem., 61 (2007) 353-398]. Beyond the more classical neoglycoproteins and glycopolymers (not covered in this work) a wide range of unprecedented and often artistically beautiful multivalent and monodisperse nanostructures, termed glycodendrimers for the first time in 1993, has been created. This chapter briefly surveys the concept of multivalency involved in carbohydrate-protein interactions. The topic is also discussed in regard to recent steps undertaken in glycobiology toward identification of lead candidates using microarrays and modern analytical tools. A systematic description of glycocluster and glycodendrimer synthesis follows, starting from the simplest architectures and ending in the most complex ones. Presentation of multivalent glycostructures of intermediate size and comprising, calix[n]arene, porphyrin, cyclodextrin, peptide, and carbohydrate scaffolds, has also been intercalated to better appreciate the growing synthetic complexity involved. A subsection describing novel all-carbon-based glycoconjugates such as fullerenes and carbon nanotubes is inserted, followed by a promising strategy involving dendrons self-assembling around metal chelates. The chapter then ends with those glycodendrimers that have been prepared using commercially available dendrimers possessing varied functionalities, or systematically synthesized using either divergent or convergent strategies.

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Section: Glycoclusters From Branched Aromatic Scaffoldsmentioning

confidence: 99%

Section: Glycoclusters From Branched Aromatic Scaffoldsmentioning

confidence: 99%

Design and Creativity in Synthesis of Multivalent Neoglycoconjugates

Chabre

Roy

2010

Advances in Carbohydrate Chemistry and Biochemistry

309

208

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“…In support of the structure of 7, there was a significant shift of the H-1 signal in its 1 H NMR spectrum: from d 6.291 (in 6) to 5.305. Finally, coupling of the isothiocyanate 7 with the amine 4 in pyridine [10] and subsequent O-deacetylation yielded the N-glucosyl thiourea derivative 8. The analytical data for 8 are in agreement with the structure and with the b-D-configuration.…”

Section: Potential Anti-tb Therapeutic Agents 1177mentioning

confidence: 99%

“…The products described in this article were obtained by the coupling of a suitably protected glycosyl isothiocyanate with p-isoamyloxyphenyl aniline (4) following the general schemes described in the literature, [9,10,12] but in several cases more efficient reagents were utilized.…”

Section: Introductionmentioning

confidence: 99%

N ‐Glycosyl‐ N ′‐[ p ‐(isoamyloxy)phenyl]‐thiourea Derivatives: Potential Anti‐TB Therapeutic Agents

Liav

Angala

Brennan

2008

Synthetic Communications

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“…The 1,3-bis(aminoethoxy)calix [4]arene with the two amino groups located at the lower rim was condensed with 2,3,4,5,6-penta-Oacetyl-d-gluconyl chloride to yield a lower-rim calix [4]arene-carbohydrate [13]. The same 1,3-bis(aminoethoxy)calix [4]arene has been employed in a coupling reaction with 2,3,4,6-tetra-O-acetyl-b-d-glucopyranosyl isothiocyanates to yield, after deprotection, a bisglycosyl-thiourea-calix [4]arene scaffold [14].…”

mentioning

confidence: 99%

Synthesis of a Novel Class of Carbohydrate-Containing Calix[4]resorcinarene Adopting an Asymmetrical Diamond Structure

Sakhaii

Verdier

Griesinger

2002

HCA

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Dedicated to Professor Dr. Dieter Seebach on the occasion of his 65th birthday A novel type of calixsugars, containing sugar moieties at the methine bridges of the calixarene is introduced. These calixsugars were prepared via a nonconvergent stepwise fragment condensation. Four new stereogenic centers were formed simultaneously, and only one diastereoisomer 5 was isolated. The condensation procedure is remarkably mild allowing for a large diversity of labile groups to be used. The solution structure of calixarene 5 with two d-glucose and two hexyl moieties was determined by NMR spectroscopy by means of NOEs and coupling constants for molecular dynamics (MD). Chemical shifts were used to validate the conformation with the least NOE and J violations. The structure of calixsugar 5 has the configuration rctc referring to one sugar residue (r reference, c cis, t trans) and adopts a diamond conformation for the macrocyclic backbone with the two sugar moieties axial on opposite sides of the macrocyclic ring and the two hexyl groups on the same side.

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Synthesis of Bridged Thiourea Calix-sugar

Abstract: The effective synthesis of a variety of bisthioureabridged calix [4]arenes substituted by carbohydrates units (D-glucose, D-mannose, D-galactose and lactose) at the narrow rim by reaction of bis(aminoethoxy)calix[4]arene 1 with glycosyl isothiocyanates is described.

Cited by 24 publications

References 29 publications

Design and Creativity in Synthesis of Multivalent Neoglycoconjugates

Design and Creativity in Synthesis of Multivalent Neoglycoconjugates

N ‐Glycosyl‐ N ′‐[ p ‐(isoamyloxy)phenyl]‐thiourea Derivatives: Potential Anti‐TB Therapeutic Agents

Synthesis of a Novel Class of Carbohydrate-Containing Calix[4]resorcinarene Adopting an Asymmetrical Diamond Structure

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