Efficient synthesis of a fluorescent tripod detection system for pesticides by microwave-assisted click chemistry

Mallard-Favier, Isabelle; Blach, Philippe; Cazier, Francine; Delattre, François

doi:10.1016/j.carres.2008.10.014

Cited by 22 publications

(20 citation statements)

References 24 publications

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“…Commercially available phloroglucinol ( 7 ) was alkylated according to a reported method 26 to produce trisalkyne 10 (Scheme 1). Using microwave-assisted copper-catalyzed azide-alkyne cycloaddition (CuAAC) reactions, the known serinamide azide 11 24 was attached to the phloroglucinol-derived hub, leading to 12a–c .…”

Section: Resultsmentioning

confidence: 99%

Trigonal scaffolds for multivalent targeting of melanocortin receptors

et al. 2015

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Melanocortin receptors can be used as biomarkers to detect and possibly treat melanoma. To these ends, molecules bearing one, two, or three copies of the weakly binding ligand MSH(4) were attached to scaffolds based on phloroglucinol, tripropargylamine, and 1,4,7-triazacyclononane by means of the copper-assisted azide-alkyne cyclization. This synthetic design allows rapid assembly of multivalent molecules. The bioactivities of these compounds were evaluated using a competitive binding assay that employed human embryonic kidney cells engineered to overexpress the melanocortin 4 receptor. The divalent molecules exhibited 10- to 30-fold higher levels of inhibition when compared to the corresponding monovalent molecules, consistent with divalent binding, whereas the trivalent molecules were only statistically (~2-fold) better than the divalent molecules, still consistent with divalent binding but inconsistent with trivalent binding. Possible reasons for these behaviors and planned refinements of the multivalent constructs targeting melanocortin receptors based on these scaffolds are discussed.

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Section: Resultsmentioning

confidence: 99%

Trigonal scaffolds for multivalent targeting of melanocortin receptors

et al. 2015

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“…Monoazidocyclodextrin has been also used in 1,3-dipolar cycloaddition with 1,3,5-tris propargylossibenzene (Scheme 15) in order to form a cyclodextrin trimer [50]. The reaction has been carried out in DMSO, under MW irradiation (80°C, 1h), using CuI as a catalyst in the presence of DIPEA.…”

Section: Saccharide Conjugation Oligo-and Polysaccharidesmentioning

confidence: 99%

Click Chemistry Under Microwave or Ultrasound Irradiation

Tagliapietra¹,

Binello²,

Cravotto

2011

COC

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The copper-catalyzed azide-alkyne cycloaddition (CuAAC) is generally recognized as the most striking example of "click reaction". CuAAC fit so well into Sharpless' definition that it became almost synonymous with "click chemistry" itself. The most common catalyst systems employ Cu(II) salt in the presence of a reducing agent (i.e. sodium ascorbate) to generate the required Cu(I) catalyst in situ or as an alternative the comproportionation of Cu(II)/Cu(0) species. Although, Cu(I) catalyzes the reaction with a rate enhancement of 10 7 even in the absence of ligands and provides a clean and selective conversion to the 1,4-substituted triazoles, some bulky and scantily reactive substrates still require long reaction times and often few side products are formed. Outstanding results have been achieved by performing CuAAC under microwave (MW) irradiation. Several authors described excellent yields, high purity and short reaction times. In few cases also power ultrasound (US) accelerated the reaction, especially when heterogeneous catalysts or metallic copper are employed. The aim of this review is to summarize and highlight the huge advantages offered by MW-and US-promoted CuAAC. In the growing scenario of innovative synthetic strategies, we intend to emphasize the complementary role played by these non-conventional energy sources and click chemistry to achieve process intensification in organic synthesis.

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“…Alkylation of 8 with propargyl bromide afforded 9 in 40 % yield. [28] The formation of 11 proceeded smoothly under standard copper-catalysed Huisgen cycloaddition conditions using four equivalents of galactose azide 10. Acid de-protection of the isopropylidene groups of 11 afforded 2 after purification by means of reverse-phase (RP)-HPLC.…”

Section: Synthesis Of Sugar Triazole Ligands 2-7mentioning

confidence: 99%

Defining the Structural Parameters of Triazole Ligands in the Templated Synthesis of Silver Nanoparticles

et al. 2014

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This manuscript describes a one-pot method for the synthesis of size-and shape-selected silver nanoparticles (AgNPs) using Tollens' reagent [Ag(NH 3 ) 2 OH] as the silver source. Sugar triazole ligands facilitate the formation of monodisperse AgNPs in which the size and shape can be controlled according to the reaction conditions. Increasing the size of the ligand reduces size tunability but enhances colloidal stability in high-salt buffers. A key conclusion from this study is

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Efficient synthesis of a fluorescent tripod detection system for pesticides by microwave-assisted click chemistry

Cited by 22 publications

References 24 publications

Trigonal scaffolds for multivalent targeting of melanocortin receptors

Trigonal scaffolds for multivalent targeting of melanocortin receptors

Click Chemistry Under Microwave or Ultrasound Irradiation

Defining the Structural Parameters of Triazole Ligands in the Templated Synthesis of Silver Nanoparticles

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