Literature DB >> 24484427

Fluorinated compounds in medicinal chemistry: recent applications, synthetic advances and matched-pair analyses.

David Barnes-Seeman, Jeremy Beck, Clayton Springer1.   

Abstract

In recent years, several new fluorinated functional groups have been employed in medicinal chemistry. This review will highlight some recent developments in this area. We draw attention to useful synthetic advances for the installation of fluorine-containing groups. In addition, we examine the application of some fluorinated functional groups that have recently been gaining popularity in drug discovery. We use matched-pair analysis to assemble aggregate data on the impact on potency of one of these groups, pentafluorosulfanyl, as compared to trifluoromethyl. We further used matchedpair analysis to identify some interesting effects on in vitro ADME properties of replacing H by F on certain moieties.

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Year:  2014        PMID: 24484427     DOI: 10.2174/1568026614666140202204242

Source DB:  PubMed          Journal:  Curr Top Med Chem        ISSN: 1568-0266            Impact factor:   3.295


  9 in total

1.  Synthesis of Trifluoromethoxylated (Hetero)Arenes via OCF3 Migration.

Authors:  Katarzyna N Lee; Johnny W Lee; Ming-Yu Ngai
Journal:  Synlett       Date:  2015-11-16       Impact factor: 2.454

2.  Structure-Activity Study of Bioisosteric Trifluoromethyl and Pentafluorosulfanyl Indole Inhibitors of the AAA ATPase p97.

Authors:  Celeste Alverez; Michelle R Arkin; Stacie L Bulfer; Raffaele Colombo; Marina Kovaliov; Matthew G LaPorte; Chaemin Lim; Mary Liang; William J Moore; R Jeffrey Neitz; Yongzhao Yan; Zhizhou Yue; Donna M Huryn; Peter Wipf
Journal:  ACS Med Chem Lett       Date:  2015-10-23       Impact factor: 4.345

3.  Opposing orientations of the anti-psychotic drug trifluoperazine selected by alternate conformations of M144 in calmodulin.

Authors:  Michael D Feldkamp; Lokesh Gakhar; Nisha Pandey; Madeline A Shea
Journal:  Proteins       Date:  2015-03-25

4.  Novel Method for Radiolabeling and Dimerizing Thiolated Peptides Using (18)F-Hexafluorobenzene.

Authors:  Orit Jacobson; Xuefeng Yan; Ying Ma; Gang Niu; Dale O Kiesewetter; Xiaoyuan Chen
Journal:  Bioconjug Chem       Date:  2015-06-24       Impact factor: 4.774

5.  [Naphthalene allyl trifluoromethyl benzocyclopentanone inhibits proliferation and induces apoptosis of lung cancer A549 cells in vitro].

Authors:  X Wu; J He; P Li; Y Wang; L Yan; J Ma
Journal:  Nan Fang Yi Ke Da Xue Xue Bao       Date:  2022-02-20

6.  Mechanistic studies on intramolecular C-H trifluoromethoxylation of (hetero)arenes via OCF3-migration.

Authors:  Katarzyna N Lee; Zhen Lei; Cristian A Morales-Rivera; Peng Liu; Ming-Yu Ngai
Journal:  Org Biomol Chem       Date:  2016-06-15       Impact factor: 3.876

Review 7.  Fluorine-18 radiochemistry, labeling strategies and synthetic routes.

Authors:  Orit Jacobson; Dale O Kiesewetter; Xiaoyuan Chen
Journal:  Bioconjug Chem       Date:  2014-12-12       Impact factor: 4.774

8.  The First Insight Into the Supramolecular System of D,L-α-Difluoromethylornithine: A New Antiviral Perspective.

Authors:  Joanna Bojarska; Roger New; Paweł Borowiecki; Milan Remko; Martin Breza; Izabela D Madura; Andrzej Fruziński; Anna Pietrzak; Wojciech M Wolf
Journal:  Front Chem       Date:  2021-05-13       Impact factor: 5.221

9.  Phenanthroline-Catalyzed Stereoselective Formation of α-1,2-cis 2-Deoxy-2-Fluoro Glycosides.

Authors:  Paul M DeMent; Chenlu Liu; Joseph Wakpal; Richard N Schaugaard; H Bernhard Schlegel; Hien M Nguyen
Journal:  ACS Catal       Date:  2021-02-02       Impact factor: 13.084

  9 in total

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