Synthesis of Glyco‐Silicas by Cu(I)‐Catalyzed “Click‐Chemistry” and their Applications in Affinity Chromatography

Ortega‐Muñoz, Mariano; Lopéz-Jaramillo, Javier; Hernandez-Mateo, Fernando; Santoyo‐González, Francisco

doi:10.1002/adsc.200790005

Cited by 7 publications

(10 citation statements)

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“…The counterparts clickable azide ( 8 – 11 ) and alkyne ( 12 – 14 ) sugars derived from monosaccharides Man and Glc, disaccharide Lac, and trivalent mannosylated dendron ( Scheme 2 ) were synthesized following methodologies previously reported. 36 , 37 Click assembly of complementary clickable triterperne ( 3 – 7 ) and sugar ( 8 – 14 ) partners was carried out in DMF using copper complex (EtO) 3 P·CuI as a soluble catalyst and under microwave irradiation (800 W, 80 °C, 15 min) to improve the yield and reduce the reaction time. 20 , 38 Saponin-like compounds 15 – 29 were thus obtained with good yield ( Scheme 3 ), and their structure was confirmed by NMR ( Figures S4–S20 ).…”

Section: Results and Discussionmentioning

confidence: 99%

Biological Evaluation and Docking Studies of Synthetic Oleanane-type Triterpenoids

et al. 2018

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Saponins are potential wide-spectrum antitumor drugs, and copper(I) catalyzed azide–alkyne 1,3-dipolar cycloaddition is a suitable approach to synthesizing saponin-like compounds by regioselective glycosylation of the C2/C3 hydroxyl and C28 carboxylic groups of triterpene aglycones maslinic acid (MA) and oleanolic acid (OA). Biological studies on the T-84 human colon carcinoma cell line support the role of the hydroxyl groups at C2/C3, the influence of the aglycone, and the bulky nature of the substituents in C28. OA bearing a α-d-mannose moiety at C28 (compound 18) focused our interest because the estimated inhibitory concentration 50 was similar to that reported for ginsenoside Rh2 against colon cancer cells and it inhibits the G1–S phase transition affecting the cell viability and apoptosis. Considering that triterpenoids from natural sources have been identified as inhibitors of nuclear factor kappa-light-chain-enhancer of activated B cell (NF-κB) signaling, docking studies were conducted to evaluate whether NF-κB may be a potential target. Results are consistent with the biological study and predict a similar binding mode of MA and compound 18 to the p52 subunit from NF-κB but not for OA. The fact that the binding site is shared by the NF-κB inhibitor 6,6-dimethyl-2-(phenylimino)-6,7-dihydrobenzo[d][1,3]oxathiol-4(5H)-one supports the result and points to NF-κB as a potential target of both MA and compound 18.

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Section: Results and Discussionmentioning

confidence: 99%

Biological Evaluation and Docking Studies of Synthetic Oleanane-type Triterpenoids

et al. 2018

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“…New glyco-silicas have shown to be efficient and valuable bioselective affinity chromatographic supports for the purification of lectins, as well as for the one-pot fluorescent labeling of these proteins. 170 Yang et al 171 developed a method, namely hydrophilic interaction chromatography (HILIC), which used a support prepared by clicking aspartic acid onto silica gel (termed as Click AA). This material was used as SP extraction sorbent for selective enrichment of glycopeptides.…”

Section: Cu(i)-catalyzed Azide−alkynementioning

confidence: 99%

CuAAC: An Efficient Click Chemistry Reaction on Solid Phase

2015

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Click chemistry is an approach that uses efficient and reliable reactions, such as Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC), to bind two molecular building blocks. CuAAC has broad applications in medicinal chemistry and other fields of chemistry. This review describes the general features and applications of CuAAC in solid-phase synthesis (CuAAC-SP), highlighting the suitability of this kind of reaction for peptides, nucleotides, small molecules, supramolecular structures, and polymers, among others. This versatile reaction is expected to become pivotal for meeting future challenges in solid-phase chemistry.

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“…Our synthesis of linear conjugated triazolylsubstituted (oligo)phenothiazine precursors for hybrid materials’ synthesis bearing triethoxylsilyl propyl groups commences from ethynylated (oligo)phenothiazines 1 [ 31 , 32 , 33 , 34 ]. Mono- and diethynylated (oligo)phenothiazines 1 undergo the CuAAC at room temp in DMF with (3-azidopropyl)tri-alkoxysilanes 2 [ 35 ] to give conjugated triazolylsubstituted (oligo)phenothiazines 3 in excellent yield as oils ( Scheme 1 ). Both triethoxy- and trimethoxysilyl derivatives 3 are readily obtained as well as methyl- and n -hexyl-substituted phenothiazine derivatives.…”

Section: Resultsmentioning

confidence: 99%

Triazolyl Conjugated (Oligo)Phenothiazines Building Blocks for Hybrid Materials—Synthesis and Electronic Properties

et al. 2021

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The Cu-catalyzed alkyne-azide 1,3-dipolar cycloaddition variant provides a highly efficient entry to conjugated triazolyl-substituted (oligo)phenothiazine organosilicon derivatives with luminescence and reversible redox characteristics. Furthermore, by in-situ co-condensation synthesis several representative mesoporous MCM-41 type silica hybrid materials with embedded (oligo)phenothiazines are prepared and characterized with respect to their structural and electronic properties. The hybrid materials also can be oxidized to covalently bound embedded radical cations, which are identified by their UV/Vis absorption signature and EPR signals.

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Synthesis of Glyco‐Silicas by Cu(I)‐Catalyzed “Click‐Chemistry” and their Applications in Affinity Chromatography

Cited by 7 publications

References 0 publications

Biological Evaluation and Docking Studies of Synthetic Oleanane-type Triterpenoids

Biological Evaluation and Docking Studies of Synthetic Oleanane-type Triterpenoids

CuAAC: An Efficient Click Chemistry Reaction on Solid Phase

Triazolyl Conjugated (Oligo)Phenothiazines Building Blocks for Hybrid Materials—Synthesis and Electronic Properties

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