1346617-84-2Relevant articles and documents
N-[2-methyl-5-(triazol-1-yl)phenyl]pyrimidin-2-amine as a Scaffold for the synthesis of inhibitors of Bcr-Abl
Arioli, Federica,Borrelli, Stella,Colombo, Francesco,Falchi, Federico,Filippi, Irene,Crespan, Emmanuele,Naldini, Antonella,Scalia, Giusy,Silvani, Alessandra,Maga, Giovanni,Carraro, Fabio,Botta, Maurizio,Passarella, Daniele
, p. 2009 - 2018 (2011)
N-[2-Methyl-5-(triazol-1-yl)phenyl]pyrimidin-2-amine derivatives were synthesized and evaluated invitro for their potential use as inhibitors of Bcr-Abl. The design is based on the bioisosterism between the 1,2,3-triazole ring and the amide group. The synthesis involves a copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) as the key step, with the exclusive production of anti-(1,4)-triazole derivatives. One of the compounds obtained shows general activity similar to that of imatinib; in particular, it was observed to be more effective in decreasing the fundamental function of cdc25A phosphatases in the K-562 cell line. Willing and Abl inhibitors! N-[2-Methyl-5-(triazol-1-yl)phenyl]pyrimidin-2-amine derivatives were synthesized by a copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) as a key step, with anti-(1,4)-triazole derivatives as the exclusive products. One of these compounds shows general activity similar to that of imatinib, and in particular, it is more effective in decreasing the fundamental function of cdc25A phosphatases in the K-562 cell line.
Modular click chemistry libraries for functional screens using a diazotizing reagent
Meng, Genyi,Guo, Taijie,Ma, Tiancheng,Zhang, Jiong,Shen, Yucheng,Sharpless, Karl Barry,Dong, Jiajia
, p. 86 - 89 (2019/11/13)
Click chemistry is a concept in which modular synthesis is used to rapidly find new molecules with desirable properties1. Copper(i)-catalysed azide–alkyne cycloaddition (CuAAC) triazole annulation and sulfur(vi) fluoride exchange (SuFEx) catalysis are widely regarded as click reactions2–4, providing rapid access to their products in yields approaching 100% while being largely orthogonal to other reactions. However, in the case of CuAAC reactions, the availability of azide reagents is limited owing to their potential toxicity and the risk of explosion involved in their preparation. Here we report another reaction to add to the click reaction family: the formation of azides from primary amines, one of the most abundant functional groups5. The reaction uses just one equivalent of a simple diazotizing species, fluorosulfuryl azide6–11 (FSO2N3), and enables the preparation of over 1,200 azides on 96-well plates in a safe and practical manner. This reliable transformation is a powerful tool for the CuAAC triazole annulation, the most widely used click reaction at present. This method greatly expands the number of accessible azides and 1,2,3-triazoles and, given the ubiquity of the CuAAC reaction, it should find application in organic synthesis, medicinal chemistry, chemical biology and materials science.
Heterocycle compound containing triazole, as well as preparation method and application of heterocycle compound
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Paragraph 0066; 0067; 0068; 0069, (2017/02/02)
The invention provides a heterocycle compound containing triazole, as well as a preparation method and application of the heterocycle compound. The heterocycle compound containing the triazole has a general formula in the following structure (as shown in
Syntheses and biological evaluation of 1,2,3-triazole and 1,3,4-oxadiazole derivatives of imatinib
Li, Yong-Tao,Wang, Jing-Han,Pan, Cheng-Wen,Meng, Fan-Fei,Chu, Xiao-Qian,Ding, Ya-Hui,Qu, Wen-Zheng,Li, Hui-Ying,Yang, Cheng,Zhang, Quan,Bai, Cui-Gai,Chen, Yue
, p. 1419 - 1427 (2016/02/19)
Three novel series of 1,2,3-triazole and 1,3,4-oxadiazole derivatives of imatinib were prepared and evaluated in vitro for their cytostatic effects against a human chronic myeloid leukemia (K562), acute myeloid leukemia (HL60), and human leukemia stem-like cell line (KG1a). The structure-activity relationship was analyzed by determining the inhibitory rate of each imatinib analog. Benzene and piperazine rings were necessary groups in these compounds for maintaining inhibitory activities against the K562 and HL60 cell lines. Introducing a trifluoromethyl group significantly enhanced the potency of the compounds against these two cell lines. Surprisingly, some compounds showed significant inhibitory activities against KG1a cells without inhibiting common leukemia cell lines (K562 and HL60). These findings suggest that these compounds are able to inhibit leukemia stem-like cells.
Safe and highly efficient syntheses of triazole drugs using Cu2O nanoparticle in aqueous solutions
Wang, Jing-Han,Pan, Cheng-Wen,Li, Yong-Tao,Meng, Fan-Fei,Zhou, Hong-Gang,Yang, Cheng,Zhang, Quan,Bai, Cui-Gai,Chen, Yue
, p. 3406 - 3409 (2013/07/19)
Triazole moiety is frequently employed in drug discovery and optimization. However, most syntheses of triazole drugs involve isolation of highly explosive azides. Herein we report safe and high efficient syntheses of triazole drugs in aqueous/organic solvent systems with Cu2O nanoparticle (Cu 2O-NP) as the catalyst of azide-alkyne cycloaddition (CuAAC). Since Cu2O-NP can be efficiently dispensed in aqueous and some organic solvents, the azide solutions from the previous preparation could be used directly in the next CuAAC stage without isolation. Therefore, this synthetic strategy is safe, convenient, and high yielding for the syntheses of triazole drugs.
