Literature DB >> 33981465

Isocyanide-Based Multicomponent Reactions of Free Phenylboronic Acids.

Constantinos G Neochoritis1,2, Tryfon Zarganes-Tzitzikas1, Michaela Novotná1, Tatiana Mitríková1, Zefeng Wang1, Katarzyna Kurpiewska3, Justyna Kalinowska-Tłuścik3, Alexander Dömling1.   

Abstract

Boronic acids are amongst the most useful synthetic intermediates, frequently used by modern drug design. However, their access and fast synthesis of libraries are often problematic. We present a methodology on the synthesis of drug-like scaffolds via IMCRs with unprotected phenylboronic acids. To demonstrate an application of our approach, we also performed one-pot Suzuki couplings on the primary MCR scaffolds. Moreover, we performed a thorough data-mining of the Cambridge Structural Database, revealing interesting geometrical features.

Entities:  

Keywords:  Boron; C-C coupling; Multicomponent reactions; Structure elucidation; Ugi reaction

Year:  2019        PMID: 33981465      PMCID: PMC8112803          DOI: 10.1002/ejoc.201901187

Source DB:  PubMed          Journal:  Eur J Chem


  29 in total

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Authors:  Alexander Dömling; Wei Wang; Kan Wang
Journal:  Chem Rev       Date:  2012-03-22       Impact factor: 60.622

2.  Decarboxylative borylation.

Authors:  Chao Li; Jie Wang; Lisa M Barton; Shan Yu; Maoqun Tian; David S Peters; Manoj Kumar; Antony W Yu; Kristen A Johnson; Arnab K Chatterjee; Ming Yan; Phil S Baran
Journal:  Science       Date:  2017-04-13       Impact factor: 47.728

Review 3.  Not boring at all. Boron is the new carbon in the quest for novel drug candidates.

Authors:  Philip Hunter
Journal:  EMBO Rep       Date:  2009-02       Impact factor: 8.807

Review 4.  Recent advances and applications of p-toluenesulfonylmethyl isocyanide (TosMIC).

Authors:  Arun Divakar Mathiyazhagan; Gopinathan Anilkumar
Journal:  Org Biomol Chem       Date:  2019-07-17       Impact factor: 3.876

5.  The role of boronic acids in accelerating condensation reactions of α-effect amines with carbonyls.

Authors:  Dennis Gillingham
Journal:  Org Biomol Chem       Date:  2016-08-10       Impact factor: 3.876

Review 6.  Recent developments with boron as a platform for novel drug design.

Authors:  Zbigniew J Leśnikowski
Journal:  Expert Opin Drug Discov       Date:  2016-04-21       Impact factor: 6.098

7.  A Multi-Component Sensor System for Detection of Amphiphilic Compounds.

Authors:  Ming Xu; Steven P Kelley; Timothy E Glass
Journal:  Angew Chem Int Ed Engl       Date:  2018-08-30       Impact factor: 15.336

8.  A New Heterocyclic Multicomponent Reaction For the Combinatorial Synthesis of Fused 3-Aminoimidazoles.

Authors:  Hugues Bienaymé; Kamel Bouzid
Journal:  Angew Chem Int Ed Engl       Date:  1998-09-04       Impact factor: 15.336

9.  Multicomponent mapping of boron chemotypes furnishes selective enzyme inhibitors.

Authors:  Joanne Tan; Armand B Cognetta Iii; Diego B Diaz; Kenneth M Lum; Shinya Adachi; Soumajit Kundu; Benjamin F Cravatt; Andrei K Yudin
Journal:  Nat Commun       Date:  2017-11-24       Impact factor: 14.919

10.  Repurposing Suzuki Coupling Reagents as a Directed Fragment Library Targeting Serine Hydrolases and Related Enzymes.

Authors:  Marion Lanier; Derek C Cole; Yelena Istratiy; Michael G Klein; Phillip A Schwartz; Richard Tjhen; Andy Jennings; Mark S Hixon
Journal:  J Med Chem       Date:  2017-06-09       Impact factor: 7.446

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  1 in total

1.  Protection-Free Strategy for the Synthesis of Boro-Depsipeptides in Aqueous Media under Microwave-Assisted Conditions.

Authors:  Shuo-Bei Qiu; Pei-Yao Liu; Bo-Cheng Wang; Pin-Rui Chen; Jing-Han Xiao; Ting-Yu Hsu; Kuan-Lin Pan; Zhi-Yin Lai; Yi-Wei Chen; Ying-Chuan Chen; Jen-Kun Chen; Po-Shen Pan
Journal:  Molecules       Date:  2022-04-04       Impact factor: 4.411

  1 in total

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