1037510-82-9Relevant academic research and scientific papers
Nickel-Catalyzed Azide-Alkyne Cycloaddition to Access 1,5-Disubstituted 1,2,3-Triazoles in Air and Water
Kim, Woo Gyum,Kang, Mi Eun,Lee, Jae Bin,Jeon, Min Ho,Lee, Sungmin,Lee, Jungha,Choi, Bongseo,Cal, Pedro M. S. D.,Kang, Sebyung,Kee, Jung-Min,Bernardes, Gon?alo J. L.,Rohde, Jan-Uwe,Choe, Wonyoung,Hong, Sung You
, p. 12121 - 12124 (2017/09/12)
Transition-metal-catalyzed or metal-free azide-alkyne cycloadditions are methods to access 1,4- or 1,5-disubstituted 1,2,3-triazoles. Although the copper-catalyzed cycloaddition to access 1,4-disubstituted products has been applied to biomolecular reaction systems, the azide-alkyne cycloaddition to access the complementary 1,5-regioisomers under aqueous and ambient conditions remains a challenge due to limited substrate scope or moisture-/air-sensitive catalysts. Herein, we report a method to access 1,5-disubstituted 1,2,3-triazoles using a Cp2Ni/Xantphos catalytic system. The reaction proceeds both in water and organic solvents at room temperature. This protocol is simple and scalable with a broad substrate scope including both aliphatic and aromatic substrates. Moreover, triazoles attached with carbohydrates or amino acids are prepared via this cycloaddition.
Synthesis and structure-activity relationship of histone deacetylase (HDAC) inhibitors with triazole-linked cap group
Chen, Po C.,Patil, Vishal,Guerrant, William,Green, Patience,Oyelere, Adegboyega K.
, p. 4839 - 4853 (2008/12/21)
Histone deacetylase (HDAC) inhibition is a recent, clinically validated therapeutic strategy for cancer treatment. Small molecule HDAC inhibitors identified so far fall in to three distinct structural motifs: the zinc-binding group (ZBG), a hydrophobic linker, and a recognition cap group. Here we report the suitability of a 1,2,3-triazole ring as a surface recognition cap group-linking moiety in suberoylanilide hydroxamic acid-like (SAHA-like) HDAC inhibitors. Using "click" chemistry (Huisgen cycloaddition reaction), several triazole-linked SAHA-like hydroxamates were synthesized. Structure-activity relationship revealed that the position of the triazole moiety as well as the identity of the cap group markedly affected the in vitro HDAC inhibition and cell growth inhibitory activities of this class of compounds.
