1267583-38-9Relevant academic research and scientific papers
A Small Library of 1,2,3-Triazole Analogs of CAP-55: Synthesis and Binding Affinity at Nicotinic Acetylcholine Receptors
Rizzi, Luca,Gotti, Cecilia,De Amici, Marco,Dallanoce, Clelia,Matera, Carlo
, (2018)
Alpha7 nicotinic acetylcholine receptor is emerging as a central regulator in inflammatory processes, as documented by increasing studies reported in the literature. For instance, the activation of this nicotinic receptor subtype in resident macrophages inhibits the production of pro-inflammatory cytokines, thereby attenuating local inflammatory responses, and may open a new window in the treatment of chronic inflammatory disease, such as Crohn's disease, rheumatoid arthritis, psoriasis, and asthma. In continuation of our ongoing research for the development of new cholinergic drug candidates, we selected the nicotine derivative CAP55, which was previously shown to exert anti-inflammatory effects via nicotinic stimulation, as a suitable compound for lead optimization. Through the isosteric replacement of its 3,5-disubstituted 4,5-dihydroisoxazole core with a 1,4-disubstituted 1,2,3-triazole ring, we could rapidly generate a small library of CAP55-related analogs via a one-pot copper(I)-catalyzed azide-alkyne cycloaddition. Receptor binding assays at nAChRs led to the identification of two promising derivatives, compounds 4 and 10, worthy of further pharmacological studies.
Novel Hybrid Thioamide Ligand Supported Copper Nanoparticles on SBA-15: A Copper Rich Robust Nanoreactor for Green Synthesis of Triazoles and Tetrazoles in Water Medium
Pourhassan, Fatemeh,Eshghi, Hossein
, p. 1287 - 1300 (2019/11/21)
Abstract: In this work, a new thioamide based ligand with reductive nature was designed for modification of mesoporous SBA-15. For this purpose, the channels of SBA-15 were modified with Tris(2-aminoethyl)amine (TAEA) groups and then reacted with S8 and phenyl acetylene to form thioamide groups via Willgerodt-Kindler reaction. This porous material proved to be an effective host for the immobilization of inexpensive Cu(II) ions. The catalytically active Cu(I) species were generated automatically due to the reductive nature of thioamide modified surface of catalyst without use of any toxic reducing agents. The well stabilized Cu(I) species into the nano-channels of SBA-15 were used for synthesis of various triazoles from sodium azide, phenyl acetylene and alkyl/benzyl halides or alkyl epoxides and various tetrazoles from sodium azide and aryl/alkyl nitriles under green mild aqueous reaction conditions. This catalytic system was used for 9 and 11 consecutive runs for synthesis of triazoles and tetrazoles, respectively. Graphic Abstract: [Figure not available: see fulltext.]
Multicomponent click reactions catalysed by copper(I) oxide nanoparticles (Cu2ONPs) derived using Oryza sativa
Chand, Dillip Kumar,Rai, Randhir
, (2020/07/10)
Abstract: A procedure for the expedient synthesis of well-characterized Cu(I) oxide nanoparticles (Cu2ONPs) from Cu(II) salts by employing Rice (Oryza sativa) as a cheap and ready source of reducing as well as stabilizing agent has been demonstrated. The judicious choice of rice as a catalyst has helped in the symbiotic combination of two events: viz., acidic hydrolysis of starch to form glucose and the subsequent formal reduction of Cu2+ by the in-situ generated monosaccharide reducing sugar (glucose) under the alkaline condition to produce Cu2O. Further, rice was also found to be effectively stabilizing the nanoparticles from agglomeration. Optical and microscopic techniques were suitably employed for the characterization of the nanoparticles of approximately 10 nm size. Furthermore, the specifically generated nanoparticles were found to be active catalysts in an aqueous medium for Azide-alkyne Huisgen cycloaddition (Click reaction) under base free condition via one-pot multi-component addition for the synthesis of mono-, bis- and tris-1,2,3-triazoles in good to excellent yields. Graphic abstract: Cu2ONPs synthesized using hydrolysed Rice, an active catalyst for synthesis of mono-, bis- and tris-1,4-disubstituted 1,2,3-triazoles via one pot multicomponent reactions in water.[Figure not available: see fulltext.].
Synthesis of click-chelator via Cu(I)-catalyzed alkyne-azide cycloaddition
Fu, Yang,Liu, Yan,Fu, Xiaoping,Zou, Li,Li, Hua,Li, Ming,Chen, Xingguo,Qin, Jingui
experimental part, p. 2226 - 2232 (2011/09/16)
The click-ligands based on 1,2,3-triazole and pyridine unit has been synthesized via Cu(I)-catalyzed alkyne-azide cycloaddition from corresponding organic azides and terminal alkynes. The ligand structure was characterized by NMR, IR and elemental analysis as well as single crystal diffractions. The single crystal structure of the complexes from two different ligands coordinating to Cu(II) and Co(II) ions indicated that the N(2) atom in 1,2,3-triazole unit can act as an efficient donor to metals through the rational molecular design. Copyright
