Condensed 1,2,3-triazoles (review)

Shafran, E. A.; Бакулев, В. А.; Rozin, Yu. A.; Shafran, Yu. M.

doi:10.1007/s10593-008-0155-9

Cited by 54 publications

(29 citation statements)

References 112 publications

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“…Recently, the click reaction has been widely used to covalently link two molecular fragments in creating a wide variety of drug-like molecules [23,24]. Typically, a terminal alkyne and an azide undergo a copper-catalyzed [3+2]-cycloaddition to generate a substituted 4β-triazole ring [25,26].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Anticancer Activity of Glucosylated Podophyllotoxin Derivatives Linked via 4β-Triazole Rings

Xu²,

et al. 2013

Molecules

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A series of 4β-triazole-linked glucose podophyllotoxin conjugates have been designed and synthesized by employing a click chemistry approach. All the compounds were evaluated for their anticancer activity against a panel of five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7, SW480) using MTT assays. Most of these triazole derivatives have good anticancer activity. Among them, compound 35 showed the highest potency against all five cancer cell lines tested, with IC 50 values ranging from 0.59 to 2.90 μM, which is significantly more active than the drug etoposide currently in clinical use. Structure-activity relationship analysis reveals that the acyl substitution on the glucose residue, the length of oligoethylene glycol linker, and the 4'-demethylation of podophyllotoxin scaffold can significantly affect the potency of the anticancer activity. Most notably, derivatives with a perbutyrylated glucose residue show much higher activity than their counterparts with either a free glucose or a peracetylated glucose residue.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Anticancer Activity of Glucosylated Podophyllotoxin Derivatives Linked via 4β-Triazole Rings

Xu²,

et al. 2013

Molecules

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“…The ability of 1,2,3-triazoles and 1,2,3-thiadiazoles to undergo various changes, particularly transformations and mutual rearrangements, has always attracted the attention of research workers [1][2][3][4][5][6][7][8][9]. 1,2,3-Triazole and 1,2,3-thiadiazole rings form part of the structure of many compounds having biological activity, and this has stimulated interest in the synthesis of new derivatives of this series.…”

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confidence: 99%

“…A broad spectrum of biological activity is also characteristic of 1,2,3-thiadiazole derivatives. Most interesting from the practical standpoint are substances having antiviral, herbicidal, and fungicidal activity and agents for the protection and growth regulation of plants [6,9,15,16].…”

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confidence: 99%

“…Only one example of the use of malonothioamides in the reaction is known -the cyclization of cyanothioacetamide in reaction with aryl azides, where the thioamide group remains unchanged [19]. This example by no means exhausts the rich chemical potentialities of thioamides, their ability to react with various electrophilic reagents and participate in various condensations [22] and rearrangements [7][8][9].…”

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confidence: 99%

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Reactions of Malonothioamide Derivatives with Azides*

Дианова

Berseneva

Eltsov

et al. 2014

Chem Heterocycl Comp

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The reactions of primary and tertiary malonothioamides with aryl and sulfonyl azides can take place in three directions, depending on the nature of the thioamides and azides. Ethoxycarbonylthioacetamide reacts with aryl azides with the formation of ethyl 5-amino-1-aryl-1,2,3-triazole-4-carboxylates. In reaction with aryl azides tertiary thioamides of cyanoacetic acid form 5-amino-1-aryl-1,2,3-triazole-4-carbothioamides, and in reaction with tosyl azide they form 5-amino-4-carboxamidino-1,2,3-thiadiazoles. Hypothetical mechanisms for the transformations are discussed.

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“…9 Accordingly, finding efficient synthesis methods of N-sulfonyltriazoles from easily accessible starting materials is a continuous necessity. Conventionally, copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) [10][11][12][13][14][15][16][17] is an efficient synthetic tool for the construction of 1,2,3-triazoles. However, the employment of sulfonyl azides resulted in apparently different outcomes and generated in situ a reactive ketenimine intermediate by ring-opening rearrangement of N-sulfonyltriazole-copper species.…”

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confidence: 99%