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Advance in Fluorine Chemistry
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Advance in Fluorine Chemistry

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Chemical Biology".

Deadline for manuscript submissions: closed (1 May 2021) | Viewed by 12613

Special Issue Editors

Prof. Dr. Steven L. Cobb

E-Mail Website
Guest Editor
Department of Chemistry, Durham University, South Road, Durham DH1 3LE, UK
Interests: chemical biology of peptides; organic synthesis; peptide and peptoid chemistry; bio-organic fluorine chemistry; bio-conjugation; drug target validation; infectious diseases and neglected tropical diseases
Special Issues, Collections and Topics in MDPI journals
Dr. Christopher R. Coxon

E-Mail Website
Guest Editor
Synthetic Chemistry Institute of Chemical Sciences, School of Engineering and Physical Sciences, Heriot-Watt University, Edinburgh EH14 4AS, UK
Interests: protein-protein interaction; proteins; organic synthesis; SDS-PAGE; enzyme activity; medicinal and pharmaceutical chemistry; synthetic medicinal chemistry; drug discovery; chromatography; heterocyclic chemistry

Special Issue Information

Dear Colleagues,

Organofluorine chemistry has played a significant role in the majority of the spectacular scientific and technological developments of the past century, although this is not widely recognised even by the scientific community. Fluoroorganic molecules are key components in an ever-increasing number of high-value commercially important products particularly in the life science industries. The use of fluorinated systems in drug discovery programmes has continued to grow and, at present, approximately 30% of new pharmaceutical and agrochemical systems that enter the market bear fluorine atoms or fluorinated substituents.

In this Special Issue, we invite research articles from colleagues working in the field of fluorine chemistry. In particular, we invite papers on the synthesis and application of new fluorinated molecules, the application of fluorine in chemical biology or medicinal chemistry, synthetic methodology for C–F bond formation, and the use of 19F NMR in biological systems.

In addition to contributing original research articles, we invite authors to submit review articles that will give the readers of Molecules updated and new perspectives on exciting emerging areas of research within the field of fluorine chemistry.

Prof. Steven L. Cobb
Dr. Christopher R. Coxon
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Published Papers (5 papers)

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Research

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17 pages, 7764 KiB  
Article
The Effect of Vicinal Difluorination on the Conformation and Potency of Histone Deacetylase Inhibitors
by A. Daryl Ariawan, Flora Mansour, Nicole Richardson, Mohan Bhadbhade, Junming Ho and Luke Hunter
Molecules 2021, 26(13), 3974; https://doi.org/10.3390/molecules26133974 - 29 Jun 2021
Cited by 2 | Viewed by 2280
Abstract
Histone deacetylase enzymes (HDACs) are potential targets for the treatment of cancer and other diseases, but it is challenging to design isoform-selective agents. In this work, we created new analogs of two established but non-selective HDAC inhibitors. We decorated the central linker chains [...] Read more.
Histone deacetylase enzymes (HDACs) are potential targets for the treatment of cancer and other diseases, but it is challenging to design isoform-selective agents. In this work, we created new analogs of two established but non-selective HDAC inhibitors. We decorated the central linker chains of the molecules with specifically positioned fluorine atoms in order to control the molecular conformations. The fluorinated analogs were screened against a panel of 11 HDAC isoforms, and minor differences in isoform selectivity patterns were observed. Full article
(This article belongs to the Special Issue Advance in Fluorine Chemistry)
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7 pages, 3760 KiB  
Article
Inter- and Intra-Molecular Organocatalysis of SN2 Fluorination by Crown Ether: Kinetics and Quantum Chemical Analysis
by Young-Ho Oh, Wonhyuck Yun, Chul-Hee Kim, Sung-Woo Jang, Sung-Sik Lee, Sungyul Lee and Dong-Wook Kim
Molecules 2021, 26(10), 2947; https://doi.org/10.3390/molecules26102947 - 15 May 2021
Cited by 4 | Viewed by 2278
Abstract
We present the intra- and inter-molecular organocatalysis of SN2 fluorination using CsF by crown ether to estimate the efficacy of the promoter and to elucidate the reaction mechanism. The yields of intramolecular SN2 fluorination of the veratrole substrates are [...] Read more.
We present the intra- and inter-molecular organocatalysis of SN2 fluorination using CsF by crown ether to estimate the efficacy of the promoter and to elucidate the reaction mechanism. The yields of intramolecular SN2 fluorination of the veratrole substrates are measured to be very small (<1% in 12 h) in the absence of crown ether promoters, whereas the SN2 fluorination of the substrate possessing a crown ether unit proceeds to near completion (~99%) in 12 h. We also studied the efficacy of intermolecular rate acceleration by an independent promoter 18-crown-6 for comparison. We find that the fluorinating yield of a veratrole substrate (leaving group = −OMs) in the presence of 18-crown-6 follows the almost identical kinetic course as that of intramolecular SN2 fluorination, indicating the mechanistic similarity of intra- and inter-molecular organocatalysis of the crown ether for SN2 fluorination. The calculated relative Gibbs free energies of activation for these reactions, in which the crown ether units act as Lewis base promoters for SN2 fluorination, are in excellent agreement with the experimentally measured yields of fluorination. The role of the metal salt CsF is briefly discussed in terms of whether it reacts as a contact ion pair or as a “free” nucleophile F−. Full article
(This article belongs to the Special Issue Advance in Fluorine Chemistry)
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16 pages, 4467 KiB  
Article
(Trifluoromethoxy)Phenylboronic Acids: Structures, Properties, and Antibacterial Activity
by Agnieszka Adamczyk-Woźniak, Jan T. Gozdalik, Ewa Kaczorowska, Krzysztof Durka, Dorota Wieczorek, Dorota Zarzeczańska and Andrzej Sporzyński
Molecules 2021, 26(7), 2007; https://doi.org/10.3390/molecules26072007 - 01 Apr 2021
Cited by 6 | Viewed by 2091
Abstract
Three isomers of (trifluoromethoxy)phenylboronic acids were studied in the context of their physicochemical, structural, antimicrobial and spectroscopic properties. They were characterized by 1H, 13C, 11B and 19F NMR spectroscopy. The acidity of all the isomers was evaluated by both [...] Read more.
Three isomers of (trifluoromethoxy)phenylboronic acids were studied in the context of their physicochemical, structural, antimicrobial and spectroscopic properties. They were characterized by 1H, 13C, 11B and 19F NMR spectroscopy. The acidity of all the isomers was evaluated by both spectrophotometric and potentiometric titrations. The introduction of the -OCF3 group influences the acidity, depending, however, on the position of a substituent, with the ortho isomer being the least acidic. Molecular and crystal structures of ortho and para isomers were determined by the single crystal XRD method. Hydrogen bonded dimers are the basic structural motives of the investigated molecules in the solid state. In the case of the ortho isomer, intramolecular hydrogen bond with the -OCF3 group is additionally formed, weaker, however, than that in the analogous -OCH3 derivative, which has been determined by both X-Ray measurements as well as theoretical DFT calculations. Docking studies showed possible interactions of the investigated compounds with LeuRS of Escherichia coli. Finally, the antibacterial potency of studied boronic acids in vitro were evaluated against Escherichia coli and Bacillus cereus. Full article
(This article belongs to the Special Issue Advance in Fluorine Chemistry)
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Review

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25 pages, 4659 KiB  
Review
Perfluoropyridine: Discovery, Chemistry, and Applications in Polymers and Material Science
by Ritesh Gautam, Ian Geniza, Scott T. Iacono, Chadron M. Friesen and Abby R. Jennings
Molecules 2022, 27(5), 1616; https://doi.org/10.3390/molecules27051616 - 28 Feb 2022
Cited by 12 | Viewed by 2244
Abstract
Perfluoropyridine (PFPy) is an organofluorine compound that has been employed for a variety of applications, from straightforward chemical synthesis to more advanced functions, such as fluorinated networks and polymers. This can be directly attributed to the highly reactive nature of PFPy, especially towards [...] Read more.
Perfluoropyridine (PFPy) is an organofluorine compound that has been employed for a variety of applications, from straightforward chemical synthesis to more advanced functions, such as fluorinated networks and polymers. This can be directly attributed to the highly reactive nature of PFPy, especially towards nucleophilic aromatic substitution (SNAr). The aim of this review is to highlight the discovery and synthesis of PFPy, discuss its reactive nature towards SNAr, and to summarize known reports of the utilization and thermal analysis of PFPy containing fluoropolymers and fluorinated network materials. Full article
(This article belongs to the Special Issue Advance in Fluorine Chemistry)
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16 pages, 4992 KiB  
Review
Current Synthetic Routes to Peptidyl Mono-Fluoromethyl Ketones (FMKs) and Their Applications
by Carissa M. Lloyd, Neil Colgin and Steven L. Cobb
Molecules 2020, 25(23), 5601; https://doi.org/10.3390/molecules25235601 - 28 Nov 2020
Cited by 3 | Viewed by 2934
Abstract
Peptidyl mono-fluoromethyl ketones (FMKs) are a class of biologically active molecules that show potential as both protease inhibitors for the treatment of a range of diseases and as chemical probes for the interrogation of cellular processes. This review describes the current solid- and [...] Read more.
Peptidyl mono-fluoromethyl ketones (FMKs) are a class of biologically active molecules that show potential as both protease inhibitors for the treatment of a range of diseases and as chemical probes for the interrogation of cellular processes. This review describes the current solid- and solution-phase routes employed for the synthesis of peptidyl mono-FMKs. In addition, it provides a brief overview of some of the key applications of FMKs in the fields of chemical biology and medicinal chemistry. Full article
(This article belongs to the Special Issue Advance in Fluorine Chemistry)
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