Synthesis of DNA-coupled isoquinolones and pyrrolidines by solid phase ytterbium- and silver-mediated imine chemistry.
作者： Marco Potowski , Verena B. K. Kunig , Florian Losch , Andreas Brunschweiger
DOI: 10.1039/C9MD00042A
关键词:
摘要: DNA-encoded libraries of chemically synthesized compounds are an important small molecule screening technology. The synthesis encoded in solution is currently restricted to a few DNA-compatible and water-tolerant reactions. Encoded compound short DNA-barcodes covalently connected solid supports benefits from broad range choices organic solvents. Here, we show that this chemistry approach allows for the DNA-coupled isoquinolones by Yb(III)-mediated Castagnoli–Cushman reaction under anhydrous conditions highly substituted pyrrolidines Ag(I)-mediated 1,3-dipolar azomethine ylide cycloaddition. An encoding scheme these DNA-barcoded based on DNA hairpin demonstrated.
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sci-hub.se 参考文章(72)
Alexander Lee Satz, Jianping Cai, Yi Chen, Robert Goodnow, Felix Gruber, Agnieszka Kowalczyk, Ann Petersen, Goli Naderi-Oboodi, Lucja Orzechowski, Quentin Strebel, DNA Compatible Multistep Synthesis and Applications to DNA Encoded Libraries Bioconjugate Chemistry. ,vol. 26, pp. 1623- 1632 ,(2015) , 10.1021/ACS.BIOCONJCHEM.5B00239
Matthew A Clark, Raksha A Acharya, Christopher C Arico-Muendel, Svetlana L Belyanskaya, Dennis R Benjamin, Neil R Carlson, Paolo A Centrella, Cynthia H Chiu, Steffen P Creaser, John W Cuozzo, Christopher P Davie, Yun Ding, G Joseph Franklin, Kurt D Franzen, Malcolm L Gefter, Steven P Hale, Nils J V Hansen, David I Israel, Jinwei Jiang, Malcolm J Kavarana, Michael S Kelley, Christopher S Kollmann, Fan Li, Kenneth Lind, Sibongile Mataruse, Patricia F Medeiros, Jeffrey A Messer, Paul Myers, Heather O'Keefe, Matthew C Oliff, Cecil E Rise, Alexander L Satz, Steven R Skinner, Jennifer L Svendsen, Lujia Tang, Kurt van Vloten, Richard W Wagner, Gang Yao, Baoguang Zhao, Barry A Morgan, Design, synthesis and selection of DNA-encoded small-molecule libraries Nature Chemical Biology. ,vol. 5, pp. 647- 654 ,(2009) , 10.1038/NCHEMBIO.211
Yujun Zhao, Liu Liu, Wei Sun, Jianfeng Lu, Donna McEachern, Xiaoqin, Li, Shanghai Yu, Denzil Bernard, Philippe Ochsenbein, Vincent Ferey, Jean-Christophe Carry, Jeffrey R. Deschamps, Duxin Sun, Shaomeng Wang, Diastereomeric spirooxindoles as highly potent and efficacious MDM2 inhibitors. Journal of the American Chemical Society. ,vol. 135, pp. 7223- 7234 ,(2013) , 10.1021/JA3125417
Samu Melkko, Jörg Scheuermann, Christoph E Dumelin, Dario Neri, Encoded self-assembling chemical libraries Nature Biotechnology. ,vol. 22, pp. 568- 574 ,(2004) , 10.1038/NBT961
Hilde van Hattum, Herbert Waldmann, Biology-oriented synthesis: harnessing the power of evolution. Journal of the American Chemical Society. ,vol. 136, pp. 11853- 11859 ,(2014) , 10.1021/JA505861D
Margit Haahr Hansen, Peter Blakskjær, Lars Kolster Petersen, Tara Heitner Hansen, Jonas Westergaard Højfeldt, Kurt Vesterager Gothelf, Nils Jakob Vest Hansen, A yoctoliter-scale DNA reactor for small-molecule evolution. Journal of the American Chemical Society. ,vol. 131, pp. 1322- 1327 ,(2009) , 10.1021/JA808558A
Nicolas Winssinger, Nucleic Acid-programmed Assemblies: Translating Instruction into Function in Chemical Biology CHIMIA International Journal for Chemistry. ,vol. 67, pp. 340- 348 ,(2013) , 10.2533/CHIMIA.2013.340
Marcos González-López, Jared T. Shaw, Cyclic anhydrides in formal cycloadditions and multicomponent reactions. Chemical Reviews. ,vol. 109, pp. 164- 189 ,(2009) , 10.1021/CR8002714
Martin J. Slater, Elizabeth M. Amphlett, David M. Andrews, Gianpaolo Bravi, George Burton, Anne G. Cheasty, John A. Corfield, Malcolm R. Ellis, Rebecca H. Fenwick, Stephanie Fernandes, Rossella Guidetti, David Haigh, C. David Hartley, Peter D. Howes, Deborah L. Jackson, Richard L. Jarvest, Victoria L. H. Lovegrove, Katrina J. Medhurst, Nigel R. Parry, Helen Price, Pritom Shah, Onkar M. P. Singh, Richard Stocker, Pia Thommes, Claire Wilkinson, Alan Wonacott, Optimization of Novel Acyl Pyrrolidine Inhibitors of Hepatitis C Virus RNA-Dependent RNA Polymerase Leading to a Development Candidate Journal of Medicinal Chemistry. ,vol. 50, pp. 897- 900 ,(2007) , 10.1021/JM061207R
S. Brenner, R. A. Lerner, Encoded combinatorial chemistry. Proceedings of the National Academy of Sciences of the United States of America. ,vol. 89, pp. 5381- 5383 ,(1992) , 10.1073/PNAS.89.12.5381