118618-40-9Relevant academic research and scientific papers
Self-Assembled Polymeric Pyridine Copper Catalysts for Huisgen Cycloaddition with Alkynes and Acetylene Gas: Application in Synthesis of Tazobactam
Hu, Hao,Ohno, Aya,Sato, Takuma,Mase, Toshiaki,Uozumi, Yasuhiro,Yamada, Yoichi M. A.
supporting information, p. 493 - 498 (2019/04/30)
Novel convoluted polymeric pyridine copper(I) catalysts PVPy-Cu were developed for the Huisgen cyclization of organic azides using alkynes and acetylene gas. They were readily prepared based on our molecular convolution of CuSO4·5H2O and poly(4-vinylpyridine) (PVPy) in the presence of sodium ascorbate with and without various sodium salts in water. Their structural investigation was conducted using XANES and EXAFS, as well as DFT calculation. The Huisgen cycloaddition of a variety of alkynes and acetylene gas was carried out using 100 to 800 mol ppm of Cu of PVPy-Cu in water, whose turnover numbers reached up to 10 000. This catalytic system was applied to the synthesis of tazobactam, which is an inhibitor of bacterial β-lactamases.
Huisgen cycloaddition with acetylene gas by using an amphiphilic self-assembled polymeric copper catalyst
Yamada, Yoichi M.A.,Yoshida, Hiroshi,Ohno, Aya,Sato, Takuma,Mase, Toshiaki,Uozumi, Yasuhiro
, p. 715 - 721 (2017/07/28)
A copper-mediated Huisgen cycloaddition, aka the copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC), of flammable acetylene gas and a variety of organic azides proceeded smoothly by using our amphiphilic self-assembled polymeric copper catalyst MPPI-C
Water-soluble NHC-Cu catalysts: Applications in click chemistry, bioconjugation and mechanistic analysis
Daz Velzquez, Heriberto,Ruiz Garca, Yara,Vandichel, Matthias,Madder, Annemieke,Verpoort, Francis
supporting information, p. 9350 - 9356 (2014/12/11)
Copper(i)-catalyzed 1,3-dipolar cycloaddition of azides and terminal alkynes (CuAAC), better known as "click" reaction, has triggered the use of 1,2,3-triazoles in bioconjugation, drug discovery, materials science and combinatorial chemistry. Here we report a new series of water-soluble catalysts based on N-heterocyclic carbene (NHC)-Cu complexes which are additionally functionalized with a sulfonate group. The complexes show superior activity towards CuAAC reactions and display a high versatility, enabling the production of triazoles with different substitution patterns. Additionally, successful application of these complexes in bioconjugation using unprotected peptides acting as DNA binding domains was achieved for the first time. Mechanistic insight into the reaction mechanism is obtained by means of state-of-the-art first principles calculations.
Synthesis and structure-activity relationship of 1- and 2-substituted-1,2,3-triazole letrozole-based analogues as aromatase inhibitors
Doiron, Jeremie,Soultan, Al Haliffa,Richard, Ryan,Toure, Mamadou Mansour,Picot, Nadia,Richard, Remi,Cuperlovic-Culf, Miroslava,Robichaud, Gilles A.,Touaibia, Mohamed
experimental part, p. 4010 - 4024 (2011/10/30)
A series of bis- and mono-benzonitrile or phenyl analogues of letrozole 1, bearing (1,2,3 and 1,2,5)-triazole or imidazole, were synthesized and screened for their anti-aromatase activities. The unsubstituted 1,2,3-triazole 10a derivative displayed inhibitory activity comparable with that of the aromatase inhibitor, letrozole 1. Compound 10a, bearing a 1,2,3-triazole, is also 10000-times more tightly binding than the corresponding analogue 25 bearing a 1,2,5-triazole, which confirms the importance of a nitrogen atom at position 3 or 4 of the 5-membered ring needed for high activity. The effect on human epithelial adrenocortical carcinoma cell line (H295R) proliferation was also evaluated. The compound 10j (IC50 = 4.64 μM), a letrozole 1 analogue bearing para-cyanophenoxymethylene-1,2,3-triazole decreased proliferation rates of H295R cells by 76 and 99% in 24 and 72 h respectively. Computer calculations, using quantum ab initio structures, suggest a possible correlation between anti-aromatase activity and the distance between the nitrogen in position 3 or 4 of triazole nitrogen and the cyano group nitrogen.
