10.1016/j.tet.2008.07.007
The study focuses on the synthesis of 1,4- and 1,5-disubstituted-1,2,3-triazolo-nucleosides from various alkynes using 10-azido-2,3,5-tri-O-acetylribose. The researchers employed copper-catalyzed azide-alkyne cycloaddition (CuAAC) and ruthenium-catalyzed azide-alkyne cycloaddition (RuAAC) methods. They optimized the RuAAC conditions using a commercially available catalyst, [Cp*RuCl(PPh3)2], under microwave heating, which significantly reduced the reaction time from 6 hours to 5 minutes and allowed the reaction to occur under water-containing conditions. Both CuAAC and RuAAC proved to be valuable tools for the synthesis of 1,2,3-triazolyl-nucleosides, which are potential therapeutic agents against DNA viruses and retroviruses, including hepatitis C virus (HCV). The synthesized compounds were evaluated for their anti-HCV activity in vitro, but none exhibited marked activity or toxicity. The study concludes that the developed methods provide an efficient approach to synthesize a small library of 1,5-disubstituted-triazolo derivatives under RuAAC and 1,4-regioisomers under CuAAC.
10.1021/jo301039y
The research focuses on the Cu(II)-promoted transformations of α-thienylcarbinols into spirothienooxindoles, which are heterocyclic compounds with potential applications in medicinal chemistry. The study aims to develop alternative synthetic methods using simple materials that efficiently introduce heteroatoms at the B-ring of spirooxindoles. The researchers have successfully converted α-thienylcarbinols with an N-phenyl carbonyl group at the other α-position into three different ranges of spirothienooxindoles, involving a dearomatizing Friedel?Crafts reaction. They also presented an unprecedented regioselective CuX2-mediated C?H functionalization/halogenation of dienyl sulfether containing electron-rich aryl rings. The chemicals used in this process include Cu(II) salts as promoters, α-thienylcarbinols as substrates, and various acids to optimize the reaction conditions. The study concluded that the combination of CuSO4·5H2O and p-TsOH was the most effective catalyst system, affording the desired spirothienooxindoles in moderate to good yields. Additionally, the researchers achieved selective halogenation of the dienyl sulfether segment, which could increase the molecular diversity and potential applications of the spirothienooxindoles. The study provides a new approach to synthesize spirothienooxindoles and expands the scope of synthetic strategies for these important heterocyclic compounds.
10.3390/molecules26030593
The research aims to develop and investigate BODIPY-peptide conjugates that target the extracellular domain of the epidermal growth factor receptor (EGFR), a receptor overexpressed in various cancers, particularly colorectal cancer (CRC). The purpose of this study is to prepare and examine the binding ability of three BODIPY-peptide conjugates to EGFR, with the ultimate goal of enhancing tumor cell specificity for cancer therapy and early detection. The researchers used copper-catalyzed click chemistry to conjugate alkynyl-functionalized BODIPY dyes with peptides modified to include an azide group, resulting in high-yield conjugates. The chemicals used in the process include BODIPY dyes 1 and 2, azido-peptides L1.5 and cycloL1.1, copper(I) sulfate pentahydrate (CuSO4·5H2O), copper(0), L-ascorbic acid, and various solvents such as tetrahydrofuran (THF) and water. The conjugates were tested for their binding affinity to EGFR using surface plasmon resonance (SPR) and for their cellular uptake and cytotoxicity in human carcinoma HEp2 cells. The study concluded that among the conjugates, those bearing an indolyl styryl group (conjugates 4 and 5) showed increased cellular uptake and cytotoxicity. Notably, conjugate 5, which contains a cyclic peptide, demonstrated the highest accumulation in EGFR-overexpressing cells, likely due to its more rigid conformation being more suitable for EGFR binding. Competitive binding studies indicated that conjugate 5 specifically binds to EGFR-overexpressing colon cancer cells, showing potential utility in in vivo imaging applications.
10.1002/anie.201706915
The research explores the first synthetic route to yndiamides, a novel class of double aza-substituted alkynes, via copper (I)-catalyzed cross-coupling of 1,1-dibromoenamides with nitrogen nucleophiles. The study aims to develop a method for preparing yndiamides and investigate their unique reactivity and potential applications in organic synthesis. The researchers optimized the coupling conditions using copper sulfate pentahydrate, 1,10-phenanthroline, and potassium phosphate, achieving high yields of yndiamides. They demonstrated the versatility of yndiamides in various transformations, including palladium-catalyzed cycloisomerizations, rhodium-catalyzed [5+2] cycloisomerizations, Pauson-Khand reactions, and Br?nsted acid-catalyzed reactions, yielding a wide range of 1,2-diamide functionalized products. The study concludes that yndiamides are valuable components in azacycle synthesis and exhibit distinct reactivity compared to ynamides, suggesting significant potential for future applications.
Xn, 
N, 
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