1,2,3‐Triazole and Its Derivatives. Development of Methods for the Formation of the Triazole Ring

Krivopalov, V. P.; Shkurko, O. P.

doi:10.1002/chin.200540270

Cited by 12 publications

(16 citation statements)

References 1 publication

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“…Since the 1,2,3-triazole ring moiety is a widespread functional group in drugs [ 25 , 26 ], the click reaction of copper-catalyzed azide-alkyne cycloaddition (CuAAC) has been widely used to covalently link two molecular fragments between a terminal alkyne and an azide to generate substituted 1,2,3-triazoles [ 27 , 28 ]. To facilitate the coupling of the sugar residue with the podophyllotoxin scaffold, a group of glycosylated terminal alkynes 12a/b – 17a/b have been prepared ( Scheme 1 ).…”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis, and Cytotoxicity of Perbutyrylated Glycosides of 4β-Triazolopodophyllotoxin Derivatives

Liu

et al. 2015

Molecules

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A series of novel perbutyrylated glycosides of 4β-triazolopodophyllotoxin derivatives were synthesized by utilizing the copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction. Evaluation of cytotoxicity against a panel of five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7, SW480) using the MTT assay shows that some of these glycosylated derivatives have good anticancer activity. Among the synthesized compounds, compound 21a shows the highest activity, with IC50 values ranging from 0.49 to 6.70 μM, which is more potent than the control drugs etoposide and cisplatin. Compound 21a is characterized by a perbutyrylated α-D(+)-galactosyl residue, the absence of an additional linking spacer between the sugar residue and the triazole ring, as well as a 4'-OH group on the E ring of the podophyllotoxin scaffold.

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Section: Resultsmentioning

confidence: 99%

Design, Synthesis, and Cytotoxicity of Perbutyrylated Glycosides of 4β-Triazolopodophyllotoxin Derivatives

Liu

et al. 2015

Molecules

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“…64 ). Among several possible ways to construct the 5-membered triazole ring, the most suitable for us was the Huisgen 1,3-dipolar cycloaddition 65 of organic azides to terminal alkynes.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antiprotozoal Activity of Cationic 1,4-Diphenyl-1H-1,2,3-triazoles

et al. 2009

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Novel dicationic triazoles 1–60 were synthesized by the Pinner method from the corresponding dinitriles, prepared via the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC). The type and the placement of cationic moieties as well as the nature of aromatic substituents influenced in vitro antiprotozoal activities of compounds 1–60 against Trypanosoma brucei rhodesiense, Plasmodium falciparum, and Leishmania donovani and their cytotoxicity for mammalian cells. Eight congeners displayed antitrypanosomal IC50 values below 10 nM. Thirty-nine dications were more potent against P. falciparum than pentamidine (IC50 = 58 nM) and eight analogues were more active than artemisinin (IC50 = 6 nM). Diimidazoline 60 exhibited antiplasmodial IC50 value of 0.6 nM. Seven congeners administered at 4 × 5 mg/kg by the intraperitoneal route cured at least three out of four animals in the acute mouse model of African trypanosomiasis. At 4 × 1 mg/kg, diamidine 46 displayed better antitrypanosomal efficacy than melarsoprol, curing all infected mice.

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“…Considering that the heterocyclic 1 H -1,2,3-triazole derivatives are structures with various properties (biological, chemical, and technical), utilizing the selective, efficient, and new catalytic systems for the production of 1 H -1,2,3-triazole compounds is an important issue in the pharmaceutical industry. 27 − 29 Lately, the Click reaction between a terminal alkyne and organic azide (CuAAC) has been found to have many uses in organic synthesis.…”

Section: Introductionmentioning

confidence: 99%

Cu-Kojic Acid Complex Anchored to Functionalized Silica-MCM-41: A Promising Regioselective and Reusable Nanocatalyst for Click Reaction

2020

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Cu-Kojic acid (KA) complex anchored to functionalized silica-MCM-41 was synthesized via the process of postgrafting and introduced as an effective, new, reusable, and thermally resistant heterogeneous nanocatalyst for the clean synthesis of 1 H -1,2,3-triazoles from Click reaction of 2-(azidomethyl)-5-benzyloxy-4-pyrone and azido Kojic acid with a variety of terminal alkynes in excellent yields. The structure of nanocatalyst was analyzed by ICP, BET, XRD, EDS, SEM, TGA, TEM, and FT-IR techniques.

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1,2,3‐Triazole and Its Derivatives. Development of Methods for the Formation of the Triazole Ring

Abstract: For Abstract see ChemInform Abstract in Full Text.

Cited by 12 publications

References 1 publication

Design, Synthesis, and Cytotoxicity of Perbutyrylated Glycosides of 4β-Triazolopodophyllotoxin Derivatives

Design, Synthesis, and Cytotoxicity of Perbutyrylated Glycosides of 4β-Triazolopodophyllotoxin Derivatives

Synthesis and Antiprotozoal Activity of Cationic 1,4-Diphenyl-1H-1,2,3-triazoles

Cu-Kojic Acid Complex Anchored to Functionalized Silica-MCM-41: A Promising Regioselective and Reusable Nanocatalyst for Click Reaction

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