Literature DB >> 30387906

Nonconjugated Hydrocarbons as Rigid-Linear Motifs: Isosteres for Material Sciences and Bioorganic and Medicinal Chemistry.

Gemma M Locke1, Stefan S R Bernhard1, Mathias O Senge1.   

Abstract

Nonconjugated hydrocarbons, like bicyclo[1.1.1]pentane, bicyclo[2.2.2]octane, triptycene, and cubane are a unique class of rigid linkers. Due to their similarity in size and shape they are useful mimics of classic benzene moieties in drugs, so-called bioisosteres. Moreover, they also fulfill an important role in material sciences as linear linkers, in order to arrange various functionalities in a defined spatial manner. In this Review article, recent developments and usages of these special, rectilinear systems are discussed. Furthermore, we focus on covalently linked, nonconjugated linear arrangements and discuss the physical and chemical properties and differences of individual linkers, as well as their application in material and medicinal sciences.
© 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

Entities:  

Keywords:  crystal engineering; electron transfer; liquid crystals; metal-organic frameworks; porphyrins

Mesh:

Substances:

Year:  2019        PMID: 30387906     DOI: 10.1002/chem.201804225

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  19 in total

1.  Quaternary Centers by Nickel-Catalyzed Cross-Coupling of Tertiary Carboxylic Acids and (Hetero)Aryl Zinc Reagents.

Authors:  Tie-Gen Chen; Haolin Zhang; Pavel K Mykhailiuk; Rohan R Merchant; Courtney A Smith; Tian Qin; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2019-01-30       Impact factor: 15.336

2.  A Radical Approach to Anionic Chemistry: Synthesis of Ketones, Alcohols, and Amines.

Authors:  Shengyang Ni; Natalia M Padial; Cian Kingston; Julien C Vantourout; Daniel C Schmitt; Jacob T Edwards; Monika M Kruszyk; Rohan R Merchant; Pavel K Mykhailiuk; Brittany B Sanchez; Shouliang Yang; Matthew A Perry; Gary M Gallego; James J Mousseau; Michael R Collins; Robert J Cherney; Pavlo S Lebed; Jason S Chen; Tian Qin; Phil S Baran
Journal:  J Am Chem Soc       Date:  2019-04-16       Impact factor: 15.419

3.  Reactions of 2-Aryl-1,3-Dithianes and [1.1.1]Propellane.

Authors:  Nisalak Trongsiriwat; Youge Pu; Yexenia Nieves-Quinones; Russell A Shelp; Marisa C Kozlowski; Patrick J Walsh
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-07       Impact factor: 15.336

4.  A General N-alkylation Platform via Copper Metallaphotoredox and Silyl Radical Activation of Alkyl Halides.

Authors:  Nathan W Dow; Albert Cabré; David W C MacMillan
Journal:  Chem       Date:  2021-06-16       Impact factor: 25.832

5.  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

6.  Photochemical Formal (4 + 2)-Cycloaddition of Imine-Substituted Bicyclo[1.1.1]pentanes and Alkenes.

Authors:  Alexander S Harmata; Taylor E Spiller; Madison J Sowden; Corey R J Stephenson
Journal:  J Am Chem Soc       Date:  2021-12-13       Impact factor: 16.383

7.  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 8.  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

9.  Electrophilic Activation of [1.1.1]Propellane for the Synthesis of Nitrogen-Substituted Bicyclo[1.1.1]pentanes.

Authors:  Sarah Livesley; Alistair J Sterling; Craig M Robertson; William R F Goundry; James A Morris; Fernanda Duarte; Christophe Aïssa
Journal:  Angew Chem Int Ed Engl       Date:  2021-11-26       Impact factor: 16.823

10.  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

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.