Ultrasound-Assisted Synthesis of 1-<i>N</i>-β-D-Glucopyranosyl-1<i>H</i>-1,2,3-triazole Benzoheterocycles and their Anti-Inflammatory Activities

Silva, Gilson B. da; Guimarães, Bruna Martins; Assis, Shalom P. O.; Lima, Vera Lúcia de Menezes; Oliveira, Ronaldo N. de

doi:10.5935/0103-5053.20130117

Cited by 5 publications

(4 citation statements)

References 2 publications

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“…Synthesis of functionalized C-glycosides through CuAAC reactions. 208 Another interesting study was reported by Silva et al 209 in 2013, which describes the synthesis of various N-glycosyl-1,2,3-triazoles from the reaction between the 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl azide and different terminal alkynes under ultrasound energy (Scheme 30). Additionally, the benzoheterocyclic conjugated compounds exhibited potent anti-inflammatory activity.…”

Section: Scheme 25mentioning

confidence: 99%

“…Synthesis of N-glycosyl-1,2,3-triazoles using ultrasonic energy. 209 In 2015 Nallapati et al 210 made changes in the structure of the antipsychotic drug olanzapine by incorporating the 1H-1,2,3-triazoles ring. The formation of this triazole unit was performed by the CuAAC reaction, using CuI and DIPEA (diisopropylethylamine) as a catalytic system and ultrasonic energy that allowed rapid access to the desired compounds (Scheme 31).…”

Section: Scheme 25mentioning

confidence: 99%

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1,2,3- Triazoles: general and key synthetic strategies

Santos¹,

Oliveira²,

Oliveira³

et al. 2020

Arkivoc

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The applications of the 1H-1,2,3-triazole derivatives are particularly attractive and have received prominent attention in scientific research. The characteristics of these heterocycles motivated the development of different strategies for their preparation and molecular diversification. Most of the synthetic procedures available in the literature are based on catalysis with copper salts. Therefore, this review has as complementary central focus and updates the information about the properties and the main methods for the preparation of 1H-1,2,3-triazole derivatives, with emphasis on methods involving 1,3-dipolar cycloaddition between organic azides and terminal alkynes catalyzed by copper.

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Section: Scheme 25mentioning

confidence: 99%

Section: Scheme 25mentioning

confidence: 99%

1,2,3- Triazoles: general and key synthetic strategies

Santos¹,

Oliveira²,

Oliveira³

et al. 2020

Arkivoc

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“…These three classes of compounds, namely 1,4-naphthoquinone, phthalimide and 1,2,3-triazole inspired our research. These moieties have biological activities against several infections [18][19][20], including ZIKV [21,22]. Our group has synthesized several heterocycle derivatives and tested their activities against human cancer cell lines [23][24][25].…”

Section: Introductionmentioning

confidence: 99%

Searching Anti-Zika Virus Activity in 1H-1,2,3-Triazole Based Compounds

et al. 2021

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Zika virus (ZIKV) is a mosquito-borne virus belonging to the Flaviviridae family and is responsible for an exanthematous disease and severe neurological manifestations, such as microcephaly and Guillain-Barré syndrome. ZIKV has a single strand positive-sense RNA genome that is translated into structural and non-structural (NS) proteins. Although it has become endemic in most parts of the tropical world, Zika still does not have a specific treatment. Thus, in this work we evaluate the cytotoxicity and antiviral activities of 14 hybrid compounds formed by 1H-1,2,3-triazole, naphthoquinone and phthalimide groups. Most compounds showed low cytotoxicity to epithelial cells, specially the 3b compound. After screening with all compounds, 4b was the most active against ZIKV in the post-infection test, obtaining a 50% inhibition concentration (IC50) of 146.0 µM and SI of 2.3. There were no significant results for the pre-treatment test. According to the molecular docking compound, 4b was suggested with significant binding affinity for the NS5 RdRp protein target, which was further corroborated by molecular dynamic simulation studies.

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“…NHC-metal complexes have received excessive attention because of wide applications in homogeneous catalysis. 1,2,3-triazoles are biologically active compounds and so they have been extensively used [2][3][4][5][6][7]. Although 1,2,3triazole heterocycle has been known since the end of the 19 th century, triazole chemistry has become popular by presenting Click chemistry concept by Sharpless group in 2001 [8].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Benzimidazolium Salts Bearing Triazole Groups

Atlı¹

2018

Celal Bayar Üniversitesi Fen Bilimleri Dergisi

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A propargyl-functionalized salt, 1-(2-methoxyethyl)-3-(prop-2-ynyl)benzimidazolium bromide (1), was prepared. 1-(2-methoxyethyl)-3-[(1-phenyl-1H-1,2,3-triazol-4-yl)methyl]benzimidazolium hexafluorophosphate (2) and 1-(2-methoxyethyl)-3-[(1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)methyl]benzimidazolium hexafluorophosphate (3) were obtained by Cu(I) catalyzed azide-alkyne cycloaddition reaction of 1 with corresponding azides. Compound 3 was transformed to 1-(2-methoxyethyl)-3-[(1-(4-aminophenyl)-1H-1,2,3triazol-4-yl)methyl]benzimidazolium hexafluorophosphate (4) by reduction reaction with hydrazine monohydrate. The structures of these propargyl-and 1,2,3-triazolyl-functionalized benzimidazolium salts were elucidated by FT-IR, 1 H NMR, 13 C NMR and elemental analysis methods.

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Ultrasound-Assisted Synthesis of 1-N-β-D-Glucopyranosyl-1H-1,2,3-triazole Benzoheterocycles and their Anti-Inflammatory Activities

Cited by 5 publications

References 2 publications

1,2,3- Triazoles: general and key synthetic strategies

1,2,3- Triazoles: general and key synthetic strategies

Searching Anti-Zika Virus Activity in 1H-1,2,3-Triazole Based Compounds

Synthesis and Characterization of Benzimidazolium Salts Bearing Triazole Groups

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