Facile synthesis of borofragments and their evaluation in activity-based protein profiling

作者: Shinya Adachi , Armand B. Cognetta 3rd , Micah J. Niphakis , Zhi He , Adam Zajdlik

DOI: 10.1039/C4CC09107H

关键词:

摘要: We describe chemistry that allows synthesis and evaluation of borofragments via conjugation of boron warheads with heterocycles of biological significance.

参考文章(46)
Stephen J. Baker, John W. Tomsho, Stephen J. Benkovic, Boron-containing inhibitors of synthetases. Chemical Society Reviews. ,vol. 40, pp. 4279- 4285 ,(2011) , 10.1039/C0CS00131G
Alexander Adibekian, Brent R Martin, Chu Wang, Ku-Lung Hsu, Daniel A Bachovchin, Sherry Niessen, Heather Hoover, Benjamin F Cravatt, Click-generated triazole ureas as ultrapotent in vivo–active serine hydrolase inhibitors Nature Chemical Biology. ,vol. 7, pp. 469- 478 ,(2011) , 10.1038/NCHEMBIO.579
Jeffrey D. St. Denis, Adam Zajdlik, Joanne Tan, Piera Trinchera, C. Frank Lee, Zhi He, Shinya Adachi, Andrei K. Yudin, Boron-Containing Enamine and Enamide Linchpins in the Synthesis of Nitrogen Heterocycles Journal of the American Chemical Society. ,vol. 136, pp. 17669- 17673 ,(2014) , 10.1021/JA510963K
K. C. Kumara Swamy, N. N. Bhuvan Kumar, E. Balaraman, K. V. P. Pavan Kumar, Mitsunobu and Related Reactions: Advances and Applications Chemical Reviews. ,vol. 109, pp. 2551- 2651 ,(2009) , 10.1021/CR800278Z
Zhi He, Piera Trinchera, Shinya Adachi, Jeffrey D. St. Denis, Andrei K. Yudin, Oxidative Geminal Functionalization of Organoboron Compounds Angewandte Chemie. ,vol. 51, pp. 11092- 11096 ,(2012) , 10.1002/ANIE.201206501
Eric M. Woerly, Jahnabi Roy, Martin D. Burke, Synthesis of most polyene natural product motifs using just 12 building blocks and one coupling reaction Nature Chemistry. ,vol. 6, pp. 484- 491 ,(2014) , 10.1038/NCHEM.1947
Reem Smoum, Abraham Rubinstein, Valery M. Dembitsky, Morris Srebnik, Boron containing compounds as protease inhibitors. Chemical Reviews. ,vol. 112, pp. 4156- 4220 ,(2012) , 10.1021/CR608202M
Eric M. Woerly, Justin R. Struble, Nagarjuna Palyam, Sean P. O’Hara, Martin D. Burke, (Z)-(2-bromovinyl)-MIDA boronate: a readily accessible and highly versatile building block for small molecule synthesis. Tetrahedron. ,vol. 67, pp. 4333- 4343 ,(2009) , 10.1016/J.TET.2011.04.021
Adam Zajdlik, Zezhou Wang, Jennifer L. Hickey, Ahmed Aman, Aaron D. Schimmer, Andrei K. Yudin, α-Boryl isocyanides enable facile preparation of bioactive boropeptides. Angewandte Chemie. ,vol. 52, pp. 8411- 8415 ,(2013) , 10.1002/ANIE.201302818
Eric P. Gillis, Martin D. Burke, Multistep synthesis of complex boronic acids from simple MIDA boronates. Journal of the American Chemical Society. ,vol. 130, pp. 14084- 14085 ,(2008) , 10.1021/JA8063759