Literature DB >> 31553875

Difluoro-Substituted Bicyclo[1.1.1]pentanes for Medicinal Chemistry: Design, Synthesis, and Characterization.

Roman M Bychek1, Valeriia Hutskalova1,2, Yuliya P Bas2, Olga A Zaporozhets2, Sergey Zozulya1,3, Vadym V Levterov1, Pavel K Mykhailiuk1,2.   

Abstract

A practical synthetic approach to the difluoro-substituted bicyclo[1.1.1]pentanes was developed. The key step was an addition of difluorocarbene (:CF2) to electron-rich bicyclo[1.1.0]butanes by the CF3TMS/NaI system. The obtained difluoro-bicyclo[1.1.1]pentanes are suggested to be used as saturated bioisosteres of benzene rings for the purpose of drug discovery projects.

Entities:  

Year:  2019        PMID： 31553875     DOI： 10.1021/acs.joc.9b01947

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  9 in total

1.  One-Pot Synthesis of Strain-Release Reagents from Methyl Sulfones.

Authors:  Myunggi Jung; Vincent N G Lindsay
Journal:  J Am Chem Soc       Date:  2022-03-14       Impact factor: 16.383

2.  Photochemical C-F Activation Enables Defluorinative Alkylation of Trifluoroacetates and -Acetamides.

Authors:  Mark W Campbell; Viktor C Polites; Shivani Patel; Juliette E Lipson; Jadab Majhi; Gary A Molander
Journal:  J Am Chem Soc       Date:  2021-11-18       Impact factor: 16.383

3.  Phenyl bioisosteres in medicinal chemistry: discovery of novel γ-secretase modulators as a potential treatment for Alzheimer's disease.

Authors:  H Ratni; K Baumann; P Bellotti; X A Cook; L G Green; T Luebbers; M Reutlinger; A F Stepan; W Vifian
Journal:  RSC Med Chem       Date:  2021-04-12

Review 4.  Put a ring on it: application of small aliphatic rings in medicinal chemistry.

Authors:  Matthias R Bauer; Paolo Di Fruscia; Simon C C Lucas; Iacovos N Michaelides; Jennifer E Nelson; R Ian Storer; Benjamin C Whitehurst
Journal:  RSC Med Chem       Date:  2021-01-07

5.  An intramolecular coupling approach to alkyl bioisosteres for the synthesis of multisubstituted bicycloalkyl boronates.

Authors:  Yangyang Yang; Jet Tsien; Jonathan M E Hughes; Byron K Peters; Rohan R Merchant; Tian Qin
Journal:  Nat Chem       Date:  2021-09-28       Impact factor: 24.427

Review 6.  Uncommon carbene insertion reactions.

Authors:  Ming-Yao Huang; Shou-Fei Zhu
Journal:  Chem Sci       Date:  2021-11-02       Impact factor: 9.825

7.  A Practical and Scalable Approach to Fluoro-Substituted Bicyclo[1.1.1]pentanes.

Authors:  Roman Bychek; Pavel K Mykhailiuk
Journal:  Angew Chem Int Ed Engl       Date:  2022-06-14       Impact factor: 16.823

8.  1,2-Difunctionalized bicyclo[1.1.1]pentanes: Long-sought-after mimetics for ortho/meta-substituted arenes.

Authors:  Jin-Xin Zhao; Yu-Xuan Chang; Chi He; Benjamin J Burke; Michael R Collins; Matthew Del Bel; Jeff Elleraas; Gary M Gallego; T Patrick Montgomery; James J Mousseau; Sajiv K Nair; Matthew A Perry; Jillian E Spangler; Julien C Vantourout; Phil S Baran
Journal:  Proc Natl Acad Sci U S A       Date:  2021-07-13       Impact factor: 11.205

Review 9.  Bridge Functionalisation of Bicyclo[1.1.1]pentane Derivatives.

Authors:  Joseph M Anderson; Nicholas D Measom; John A Murphy; Darren L Poole
Journal:  Angew Chem Int Ed Engl       Date:  2021-08-07       Impact factor: 16.823
  9 in total

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