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

被引：84

作者：

Bychek, Roman ^{[1
]}

Mykhailiuk, Pavel K. ^{[1
]}

机构：

[1] Enamine Ltd, Chervonotkatska 60, UA-02094 Kiev, Ukraine

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2022年 / 61卷 / 29期

基金：

欧洲研究理事会;

关键词：

Bicyclo[1; 1; 0]butane; 1]pentane; Bioisosteres; Fluorine; CHEMISTRY; PEPTIDE; DESIGN;

D O I：

10.1002/anie.202205103

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

After more than 20 years of trials, a practical scalable approach to fluoro-substituted bicyclo[1.1.1]pentanes (F-BCPs) has been developed. The physicochemical properties of the F-BCPs have been studied, and the core was incorporated into the structure of the anti-inflammatory drug Flurbiprofen in place of the fluorophenyl ring.

引用

页数：7

共 87 条

[1] CROSS CAGE INTERACTIONS IN SUBSTITUTED BICYCLO[1.1.1]PENT-1-YL RADICALS - DISSOCIATION TO [1.1.1]PROPELLANE [J].

ADCOCK, W ;

BINMORE, GT ;

KRSTIC, AR ;

WALTON, JC ;

WILKIE, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (10) :2758-2766

[2]

Anderson J. M., 2021, Angewandte Chemie, V133, P24958

[3] Bridge Functionalisation of Bicyclo[1.1.1]pentane Derivatives [J].

Anderson, Joseph M. ;

Measom, Nicholas D. ;

Murphy, John A. ;

Poole, Darren L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (47) :24754-24769

[4]

[Anonymous], 2017, ANGEW CHEM, V129, P12949

[5]

[Anonymous], 2020, ANGEW CHEM, V132, P3945

[6]

[Anonymous], 2016, ANGEW CHEM, V128, P15008

[7]

[Anonymous], 2020, ANGEW CHEM, V132, P20412

[8]

APPLEQUIST DE, 1977, TETRAHEDRON LETT, P3411

[9] POLAR SUBSTITUENT EFFECTS IN 1,3-DISUBSTITUTED BICYCLO[1.1.1]PENTANES [J].

APPLEQUIST, DE ;

RENKEN, TL ;

WHEELER, JW .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (25) :4985-4995

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

Bychek, Roman M. ;

Hutskalova, Valeriia ;

Bas, Yuliya P. ;

Zaporozhets, Olga A. ;

Zozulya, Sergey ;

Levterov, Vadym V. ;

Mykhailiuk, Pavel K. .

JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (23) :15106-15117

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