A new solvent system for efficient synthesis of 1,2,3-triazoles

Lee, Bo-Young; Park, Sora; Jeon, Heung Bae; Kim, Kwan Soo

doi:10.1016/j.tetlet.2006.05.079

Cited by 162 publications

(86 citation statements)

References 28 publications

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“…Most probably the 5-hexynyl group is not reactive enough to link two large molecules such as the oligonucleotides, but it may be used for linking small organic molecules to oligonucleotides. This result is in agreement with Click reactions involving alkynes without a neighbouring electron-withdrawing group [28,29].…”

Section: Cu-catalyzed Cycloaddition Of Azido-oligonucleotides and Alksupporting

confidence: 90%

Synthesis of Oligonucleotides Carrying 5′‐5′ Linkages Using Copper‐Catalyzed Cycloaddition Reactions

Alvira

Eritja²

2007

Chemistry & Biodiversity

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There is considerable interest in coupling oligonucleotides to molecules and surfaces.Although amino-and thiol-containing oligonucleotides are being successfully used for this purpose, cycloaddition reactions may offer greater advantages due to their higher chemoselectivity and speed. In this study, copper-catalyzed 1,3-dipolar cycloaddition reactions between oligonucleotides carrying azido and alkyne groups are examined. For this purpose several protocols for the preparation of oligonucleotides carrying these two groups are described. The non-templated chemical ligation of two oligonucleotides via coppercatalyzed [3+2] cycloaddition is described. Using solid-phase methodology oligonucleotides carrying 5'-5' linkages can be obtained in good yields.--

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Section: Cu-catalyzed Cycloaddition Of Azido-oligonucleotides and Alksupporting

confidence: 90%

Synthesis of Oligonucleotides Carrying 5′‐5′ Linkages Using Copper‐Catalyzed Cycloaddition Reactions

Alvira

Eritja²

2007

Chemistry & Biodiversity

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“…Room-temperature click reactions have been described for a 1:1:1 solvent mixture of tBuOH/H 2 O/CH 2 Cl 2 . [18] With these reaction conditions we observed conversion to 3 in 93 % yield.…”

mentioning

confidence: 71%

Construction and Screening of a 2‐Aminoimidazole Library Identifies a Small Molecule Capable of Inhibiting and Dispersing Bacterial Biofilms across Order, Class, and Phylum

Rogers

Melander

2008

Angewandte Chemie

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“…29,30 Ethynyl-1,2,3-trimethoxybenzene 25d was synthesized by the Corey-Fuchs method (Scheme 1). 25,31 Next, the aromatic azides 27a-d were prepared by the reaction of aromatic amines 26a-d with t-BuONO/TMSN 3 using the protocol reported by Moses and co-workers 33 (Scheme 2 Compounds 17, 18 and 19 were more active against L. amazonenis than was pentamidine (IC 50 8.9 μM). Compound 17, an analogue of machilin G 3, was 8 times more active than pentamidine, while 18 and 19 were 2.5 and 1.2 times more active than pentamidine, respectively ( Table 2).…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and Antitrypanosomastid Activity of 1,4-Diaryl-1,2,3-triazole Analogues of Neolignans Veraguensin, Grandisin and Machilin G

Cassamale¹,

Costa²,

Carvalho³

et al. 2016

Journal of the Brazilian Chemical Society

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Sixteen 1,4-diaryl-1,2,3-triazole compounds derived from the natural products veraguensin, grandisin and machilin G were synthesized, with yields of 78-92%. Biological activity tests against Leishmania amazonensis promastigotes showed that three of these compounds were the most active, with maximum inhibitory concentration (IC 50 ) values of 1.1, 3.71 and 7.23 µM. One compound was highly active against Leishmania infantum, with an IC 50 value of 5.2 µM, and one derivative showed an IC 50 value of 28.6 µM against Trypanosoma cruzi trypomastigotes. Regarding structureactivity relationship (SAR), hybrid 1,2,3-triazolic compounds containing a methylenedioxy group, showed the best antileishmanial and antitrypanosomal activities.

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A new solvent system for efficient synthesis of 1,2,3-triazoles

Cited by 162 publications

References 28 publications

Synthesis of Oligonucleotides Carrying 5′‐5′ Linkages Using Copper‐Catalyzed Cycloaddition Reactions

Synthesis of Oligonucleotides Carrying 5′‐5′ Linkages Using Copper‐Catalyzed Cycloaddition Reactions

Construction and Screening of a 2‐Aminoimidazole Library Identifies a Small Molecule Capable of Inhibiting and Dispersing Bacterial Biofilms across Order, Class, and Phylum

Synthesis and Antitrypanosomastid Activity of 1,4-Diaryl-1,2,3-triazole Analogues of Neolignans Veraguensin, Grandisin and Machilin G

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