28798-81-4Relevant articles and documents
Mechanochemical click reaction as a tool for making carbohydrate-based triazole-linked self-assembling materials (CTSAMs)
Tyagi, Mohit,Taxak, Nikhil,Bharatam, Prasad V.,Nandanwar, Hemraj,Kartha, K.P. Ravindranathan
, p. 137 - 147 (2015)
Various glycosides in which glycosylated triazole residues are anchored on to a central phenyl ring have been prepared under green reaction conditions by a solvent-free mechanochemical method. Some of the glycosides exhibited the ability to form gels when in contact with long chain hydrocarbons, e.g. hexane, heptane and octane, and this property was phase-selective. Thus, from a mixture of hexane-water, the compounds preferably absorbed the alkane to form a gel. The gelation ability was found to increase with an increasing number of substituents on the phenyl ring but only up to tetra-substitution. The hexa-substituted phenyl derivative did not swell in the hydrocarbon solvents investigated. The spontaneous self-assembling properties of these compounds in hexane have been investigated by transmission electron microscopy (TEM). Molecular modelling was used to optimize the structural geometry of these carbohydrate-based triazole-linked self-assembling materials (CTSAMs) and to rationalize their behaviour.
Anti-Lung Cancer Activities of 1,2,3-Triazole Curcumin Derivatives via Regulation of the MAPK/NF-κB/STAT3 Signaling Pathways
Zhi, Tai Xin,Liu, Kai Qiang,Cai, Kun Yi,Zhao, Yu Chao,Li, Zhen Wang,Wang, Xin,He, Xin Hua,Sun, Xian Yu
, (2021/12/01)
In this study, a series of curcumin derivatives containing 1,2,3-triazole were designed and synthesized, and their inhibitory activities against the proliferation of lung cancer cells were studied. Compound 5 k (3,4-dichlorobenzyltriazole methyl curcumin)
Pyridinyl-triazole ligand systems for highly efficient CuI-catalyzed azide-alkyne cycloaddition
Chen, Yunfeng,Meng, Xianggao,Wang, Ye,Zheng, Lei
, (2020/10/02)
Pyridinyl-triazole ligand systems (including N2-2-pyridinyl 1,2,3-triazoles and N1/N2-substituted 2-(NH-1,2,3-triazol-4-yl)pyridines) were found to be superior ligands for CuI-catalyzed azide-alkyne cycloaddition (CuAAC) r
Copper(ii) complexes ofN-propargyl cyclam ligands reveal a range of coordination modes and colours, and unexpected reactivity
Counsell, Andrew J.,Yu, Mingfeng,Shi, Mengying,Jones, Angus T.,Batten, James M.,Turner, Peter,Todd, Matthew H.,Rutledge, Peter J.
supporting information, p. 3931 - 3942 (2021/03/29)
The coordination chemistry ofN-functionalised cyclam ligands has a rich history, yet cyclam derivatives with pendant alkynes are largely unexplored. This is despite the significant potential and burgeoning application ofN-propargyl cyclams and related com
Tuning the optical properties of BODIPY dyes by N-rich heterocycle conjugation using a combined synthesis and computational approach
Banala, Srinivas,Kiessling, Fabian,Merkes, Jean Michel,Ostlender, Tobias,Sun, Haitao,Wang, Fufang
supporting information, p. 19641 - 19645 (2021/11/12)
The increased number of N-atoms induced a blueshift in absorption and a gain in fluorescence quantum yield, from 750 nm and ～0% for pyrrole to 635 nm and ～40% for triazole, respectively. DFT calculations indicated a decrease in HOMO energy levels with the
Tris-isocyanide copper(I) complex enabling copper azide-alkyne cycloaddition in neat conditions
Ferraro, Valentina,Sole, Roberto,Bortoluzzi, Marco,Beghetto, Valentina,Castro, Jesús
, (2021/08/13)
The three-coordinated homoleptic Cu(I) complex with 2,6-dimethylphenyl isocyanide in the coordination sphere was easily synthesized and isolated as tetrafluoroborate salt. The structure of the compound was determined by single-crystal X-ray diffraction. T
Regioselective reduction of 1h-1,2,3-triazole diesters
Butler, Christopher R.,Bendesky, Justin,Schoffstall, Allen Milton
, (2021/09/24)
Regioselective reactions can play pivotal roles in synthetic organic chemistry. The reduction of several 1-substituted 1,2,3-triazole 4,5-diesters by sodium borohydride has been found to be regioselective, with the C(5) ester groups being more reactive towards reduction than the C(4) ester groups. The amount of sodium borohydride and reaction time required for reduction varied greatly depending on the N(1)-substituent. The presence of a β-hydroxyl group on the N(1)-substituent was seen to have a rate enhancing effect on the reduction of the C(5) ester group. The regioselective reduction was attributed to the lower electron densities of the C(5) and the C(5) ester carbonyl carbon of the 1,2,3-triazole, which were further lowered in cases involving intramolecular hydrogen bonding.
Immobilized galactose oxidase in alginate gel (GO-Bead): a versatile and efficient biocatalyst for the regioselective synthesis of 1,4-disubstitued-1,2,3-triazoles: click reaction
Akbari Gourdani, Fateme,Ghadam, Parinaz,Heravi, Majid M.,Malmir, Masoume
, p. 1471 - 1478 (2021/01/09)
Galactose oxidase (E.C. 1.1.3.9) is an extracellular oxidoreductase enzyme containing Cu(I) which is produced by some fungi like Fusarium species. The enzyme catalyzes the selective oxidation of primary alcohols like galactose. In this study, a heterogeneous enzymatic system for click reaction was prepared. The most important advantage of the heterogeneous catalyst is the ease of separation and their possible reusability. Therefore, galactose oxidase was immobilized by entrapment; for this purpose, alginate polysaccharide beads with different diameters were synthesized and galactose oxidase was immobilized into them to obtain galactose oxidase-bead (GO-Bead). Next, the catalytic activity of galactose oxidase-beads was examined in the one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles via click reaction comprising diversely benzyl halides, sodium azide and different alkynes in aqueous medium which need Cu(I) for their performance. The catalyst was conventionally recovered and effectively reused in several runs with no appreciable decrease in its catalytic activity.
Pyrazine Based Type-I Sensitizing Assemblies for Photoreduction of Cu(II) in ‘One-Pot Three-Component’ CuAAC Reaction Under Aerial Conditions
Kumar, Sourav,Kumar, Manoj,Bhalla, Vandana
supporting information, p. 3944 - 3950 (2021/10/19)
Photosensitizing assemblies of pyrazine derivative PDA have been developed which exhibit a high photostability, ‘lighted’ excited state, balanced redox potential, high transportation potential and activate oxygen via type-I pathway only. These PDA assemblies in combination with Cu(II) ions catalyze the CuAAC reaction via in situ reduction of Cu(II) ions without any reducing or stabilizing agent. The present protocol has wide substrate scope with recyclability of the catalytic system up to six catalytic cycles and is applicable to gram-scale synthesis.
Catalytic performance of Cu(II)-supported graphene quantum dots modified NiFe2O4 as a proficient nano-catalyst in the synthesis of 1,2,3-triazoles
Deilam, Razieh,Moeinpour, Farid,Mohseni-Shahri, Fatemeh S.
, (2020/07/06)
Abstract: NiFe2O4 nanoparticles are modified by graphene quantum dots (GQDs) and utilized to stabilize the Cu(II) nanoparticles as a novel magnetically retrievable catalytic system (Cu(II)/GQDs/NiFe2O4) for gree
