The expanding reaction toolkit for DNA-encoded libraries

被引:68
作者
Fair, Richard J. [1 ]
Walsh, Ryan T. [1 ]
Hupp, Christopher D. [1 ]
机构
[1] X Chem Inc, 100 Beaver St, Waltham, MA 02453 USA
关键词
DNA-encoded libraries; Combinatorial chemistry; Drug discovery; Hit identification; Medicinal chemistry; SOLID-PHASE SYNTHESIS; DESIGN; HETEROCYCLES; DISCOVERY; SELECTION; CYCLOADDITION; ALKYLATION; INHIBITORS; REDUCTION; CHEMISTRY;
D O I
10.1016/j.bmcl.2021.128339
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Over the past decade, DNA-encoded libraries (DELs) have emerged as a leading platform for small molecule drug discovery among pharmaceutical companies, biotech companies and academic drug hunters alike. This revolutionary technology has tremendous potential that is yet to be fully realized, as the exploration of therapeutically relevant chemical space is fueled by the ever-expanding repertoire of DNA-compatible reactions used to construct the libraries. Advances in direct coupling reactions, like photo-catalytic cross couplings, unique cyclizations such as the formation of 1,2,4-oxadiazoles, and new functional group transformations are valuable contributions to the DEL reaction toolkit, and indicate where future reaction development efforts should focus in order to maximize the productivity of DELs.
引用
收藏
页数:24
相关论文
共 118 条
[81]   Discovery of a Highly Selective BET BD2 Inhibitor from a DNA-Encoded Library Technology Screening Hit [J].
Rianjongdee, Francesco ;
Atkinson, Stephen J. ;
Chung, Chun-Wa ;
Grandi, Paola ;
Gray, James R. J. ;
Kaushansky, Laura J. ;
Medeiros, Patricia ;
Messenger, Cassie ;
Phillipou, Alex ;
Preston, Alex ;
Prinjha, Rab K. ;
Rioja, Inmaculada ;
Satz, Alexander L. ;
Taylor, Simon ;
Wall, Ian D. ;
Watson, Robert J. ;
Yao, Gang ;
Demont, Emmanuel H. .
JOURNAL OF MEDICINAL CHEMISTRY, 2021, 64 (15) :10806-10833
[82]   An Amphiphilic Polymer-Supported Strategy Enables Chemical Transformations under Anhydrous Conditions for DNA-Encoded Library Synthesis [J].
Ruff, Yves ;
Martinez, Roberto ;
Pelle, Xavier ;
Nimsgern, Pierre ;
Fille, Pascale ;
Ratnikov, Maxim ;
Berst, Frederic .
ACS COMBINATORIAL SCIENCE, 2020, 22 (03) :120-128
[83]   Efficient copper-catalyzed amination of DNA-conjugated aryl iodides under mild aqueous conditions [J].
Ruff, Yves ;
Berst, Frederic .
MEDCHEMCOMM, 2018, 9 (07) :1188-1193
[84]   DNA Compatible Multistep Synthesis and Applications to DNA Encoded Libraries [J].
Satz, Alexander Lee ;
Cai, Jianping ;
Chen, Yi ;
Goodnow, Robert ;
Gruber, Felix ;
Kowalczyk, Agnieszka ;
Petersen, Ann ;
Naderi-Oboodi, Goli ;
Orzechowski, Lucja ;
Strebel, Quentin .
BIOCONJUGATE CHEMISTRY, 2015, 26 (08) :1623-1632
[85]   DNA-encoded libraries (DELs): a review of on-DNA chemistries and their output [J].
Shi, Ying ;
Wu, Yan-ran ;
Yu, Jian-qiang ;
Zhang, Wan-nian ;
Zhuang, Chun-lin .
RSC ADVANCES, 2021, 11 (04) :2359-2376
[86]   Solid-Phase Synthesis of β-Hydroxy Ketones Via DNA-Compatible Organocatalytic Aldol Reactions [J].
Shu, Keitou ;
Kodadek, Thomas .
ACS COMBINATORIAL SCIENCE, 2018, 20 (05) :277-281
[87]   One-Step Synthesis of Saturated Spirocyclic N-Heterocycles with Stannyl Amine Protocol (SnAP) Reagents and Ketones [J].
Siau, Woon-Yew ;
Bode, Jeffrey W. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (51) :17726-17729
[88]   Micellar Bronsted Acid Mediated Synthesis of DNA-Tagged Heterocycles [J].
Skopic, M. Klika ;
Goette, K. ;
Gramse, C. ;
Dieter, M. ;
Pospich, S. ;
Raunser, S. ;
Weberskirch, R. ;
Brunschweiger, A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (26) :10546-10555
[89]  
Skopic MK, 2017, ORG BIOMOL CHEM, V15, P8648, DOI [10.1039/c7ob02347brsc.li/obc, 10.1039/c7ob02347b]
[90]   Acid- and Au(I)-mediated synthesis of hexathymidine-DNA-heterocycle chimeras, an efficient entry to DNA-encoded libraries inspired by drug structures [J].
Skopic, Mateja Klika ;
Salamon, Hazem ;
Bugain, Olivia ;
Jung, Kathrin ;
Gohla, Anne ;
Doetsch, Lara J. ;
dos Santos, Denise ;
Bhat, Avinash ;
Wagner, Bernd ;
Brunschweiger, Andreas .
CHEMICAL SCIENCE, 2017, 8 (05) :3356-3361