Literature DB >> 31066567

Chemoselective Synthesis of Lenalidomide-Based PROTAC Library Using Alkylation Reaction.

Xing Qiu1, Ning Sun2, Ying Kong2, Yan Li2, Xiaobao Yang2, Biao Jiang1,2.   

Abstract

An organic base-promoted chemoselective alkylation of lenalidomide with different halides was developed, which offers a novel approach to a highly functionalized lenalidomide-based PROTAC library under mild reaction conditions. DIPEA was found to act as an efficient base to trigger facile generation of arylamine alkylation products compared with inorganic bases. This library was successfully applied to BET PROTAC, which not only degraded BET protein but also effectively inhibited cancer cell proliferation.

Entities:  

Year:  2019        PMID： 31066567     DOI： 10.1021/acs.orglett.9b01326

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  8 in total

1.  H· Transfer-Initiated Synthesis of γ-Lactams: Interpretation of Cycloisomerization and Hydrogenation Ratios.

Authors:  Chris Lorenc; Hunter B Vibbert; Chengbo Yao; Jack R Norton; Michael Rauch
Journal:  ACS Catal       Date:  2019-10-09       Impact factor: 13.084

2.  Discovery of a First-in-Class Degrader for Nuclear Receptor Binding SET Domain Protein 2 (NSD2) and Ikaros/Aiolos.

Authors:  Fanye Meng; Chenxi Xu; Kwang-Su Park; H Ümit Kaniskan; Gang Greg Wang; Jian Jin
Journal:  J Med Chem       Date:  2022-07-27       Impact factor: 8.039

3.  Development of Rapid and Facile Solid-Phase Synthesis of PROTACs via a Variety of Binding Styles.

Authors:  Hanqiao Xu; Takashi Kurohara; Reina Takano; Hidetomo Yokoo; Norihito Shibata; Nobumichi Ohoka; Takao Inoue; Mikihiko Naito; Yosuke Demizu
Journal:  ChemistryOpen       Date:  2022-07       Impact factor: 2.630

4.  A platform for the rapid synthesis of proteolysis targeting chimeras (Rapid-TAC) under miniaturized conditions.

Authors:  Le Guo; Yaxian Zhou; Xueqing Nie; Zhongrui Zhang; Zhen Zhang; Chunrong Li; Taobo Wang; Weiping Tang
Journal:  Eur J Med Chem       Date:  2022-04-01       Impact factor: 7.088

5.  Traceless Staudinger ligation enabled parallel synthesis of proteolysis targeting chimera linker variants.

Authors:  Troy A Bemis; James J La Clair; Michael D Burkart
Journal:  Chem Commun (Camb)       Date:  2021-01-06       Impact factor: 6.222

Review 6.  Current strategies for the design of PROTAC linkers: a critical review.

Authors:  Robert I Troup; Charlene Fallan; Matthias G J Baud
Journal:  Explor Target Antitumor Ther       Date:  2020-10-30

7.  Design, Synthesis and Biological Characterization of Histone Deacetylase 8 (HDAC8) Proteolysis Targeting Chimeras (PROTACs) with Anti-Neuroblastoma Activity.

Authors:  Salma Darwish; Ehab Ghazy; Tino Heimburg; Daniel Herp; Patrik Zeyen; Rabia Salem-Altintas; Johannes Ridinger; Dina Robaa; Karin Schmidtkunz; Frank Erdmann; Matthias Schmidt; Christophe Romier; Manfred Jung; Ina Oehme; Wolfgang Sippl
Journal:  Int J Mol Sci       Date:  2022-07-07       Impact factor: 6.208

Review 8.  E3 Ligase Ligands in Successful PROTACs: An Overview of Syntheses and Linker Attachment Points.

Authors:  Aleša Bricelj; Christian Steinebach; Robert Kuchta; Michael Gütschow; Izidor Sosič
Journal:  Front Chem       Date:  2021-07-05       Impact factor: 5.221
  8 in total

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