European Journal of Medicinal Chemistry, volume 186, pages 111826

Applications of fluorine-containing amino acids for drug design

Mei Haibo ¹

Han Jianlin ¹

Klika Karel D. ²

Izawa Kunisuke ³

SATO Tatsunori ³

Meanwell Nicholas A. ⁴

Soloshonok Vadim A. ^{5, 6}

Hide authors affiliations Show authors affiliations: 6 affiliations

College of Chemical Engineering Nanjing Forestry University, Nanjing 210037, China. |

Molecular Structure Analysis, German Cancer Research Center (DKFZ), Im Neuenheimer Feld 280, D-69120 Heidelberg, Germany |

Hamari Chemicals Ltd., 1-4-29 Kunijima, Higashi-Yodogawa-ku, Osaka, 533-0024, Japan. |

⁴

Department of Discovery Chemistry, Bristol-Myers Squibb Research and Development, PO Box 4000, Princeton, NJ, 08543-4000, United States |

⁵

Department of Organic Chemistry I, University of the Basque Country UPV/EHU, Paseo Manuel Lardizábal 3, 20018, San Sebastián, Spain |

⁶

IKERBASQUE, Basque Foundation for Science, María Díaz de Haro 3, Plaza Bizkaia, 48013, Bilbao, Spain |

Publication type: Journal Article

Publication date: 2020-01-01

Elsevier

Journal: European Journal of Medicinal Chemistry

Quartile SCImago

Quartile WOS

Impact factor: 6.7

ISSN: 02235234, 17683254

DOI: 10.1016/j.ejmech.2019.111826

Copy DOI

Organic Chemistry

Drug Discovery

General Medicine

Pharmacology

Abstract

Fluorine-containing amino acids are becoming increasingly prominent in new drugs due to two general trends in the modern pharmaceutical industry. Firstly, the growing acceptance of peptides and modified peptides as drugs; and secondly, fluorine editing has become a prevalent protocol in drug-candidate optimization. Accordingly, fluorine-containing amino acids represent one of the more promising and rapidly developing areas of research in organic, bio-organic and medicinal chemistry. The goal of this Review article is to highlight the current state-of-the-art in this area by profiling 42 selected compounds that combine fluorine and amino acid structural elements. The compounds under discussion represent pharmaceutical drugs currently on the market, or in clinical trials as well as examples of drug-candidates that although withdrawn from development had a significant impact on the progress of medicinal chemistry and/or provided a deeper understanding of the nature and mechanism of biological action. For each compound, we present features of biological activity, a brief history of the design principles and the development of the synthetic approach, focusing on the source of tailor-made amino acid structures and fluorination methods. General aspects of the medicinal chemistry of fluorine-containing amino acids and synthetic methodology are briefly discussed.

By date By citations

Citations by journals

	1 2 3 4 5 6 7 8
Molecules	Molecules, 8, 5.16% Molecules 8 publications, 5.16%
Journal of Fluorine Chemistry	Journal of Fluorine Chemistry, 7, 4.52% Journal of Fluorine Chemistry 7 publications, 4.52%
European Journal of Organic Chemistry	European Journal of Organic Chemistry, 7, 4.52% European Journal of Organic Chemistry 7 publications, 4.52%
Journal of Organic Chemistry	Journal of Organic Chemistry, 7, 4.52% Journal of Organic Chemistry 7 publications, 4.52%
Organic and Biomolecular Chemistry	Organic and Biomolecular Chemistry, 5, 3.23% Organic and Biomolecular Chemistry 5 publications, 3.23%
Angewandte Chemie	Angewandte Chemie, 5, 3.23% Angewandte Chemie 5 publications, 3.23%
Chinese Chemical Letters	Chinese Chemical Letters, 5, 3.23% Chinese Chemical Letters 5 publications, 3.23%
Chirality	Chirality, 5, 3.23% Chirality 5 publications, 3.23%
Chemistry - A European Journal	Chemistry - A European Journal, 5, 3.23% Chemistry - A European Journal 5 publications, 3.23%
Angewandte Chemie - International Edition	Angewandte Chemie - International Edition, 5, 3.23% Angewandte Chemie - International Edition 5 publications, 3.23%
Organic Letters	Organic Letters, 5, 3.23% Organic Letters 5 publications, 3.23%
Organic Chemistry Frontiers	Organic Chemistry Frontiers, 5, 3.23% Organic Chemistry Frontiers 5 publications, 3.23%
Advanced Synthesis and Catalysis	Advanced Synthesis and Catalysis, 4, 2.58% Advanced Synthesis and Catalysis 4 publications, 2.58%
European Journal of Medicinal Chemistry	European Journal of Medicinal Chemistry, 4, 2.58% European Journal of Medicinal Chemistry 4 publications, 2.58%
ACS Catalysis	ACS Catalysis, 3, 1.94% ACS Catalysis 3 publications, 1.94%
Beilstein Journal of Organic Chemistry	Beilstein Journal of Organic Chemistry, 3, 1.94% Beilstein Journal of Organic Chemistry 3 publications, 1.94%
International Journal of Molecular Sciences	International Journal of Molecular Sciences, 3, 1.94% International Journal of Molecular Sciences 3 publications, 1.94%
ChemistrySelect	ChemistrySelect, 3, 1.94% ChemistrySelect 3 publications, 1.94%
Chemical Science	Chemical Science, 3, 1.94% Chemical Science 3 publications, 1.94%
Symmetry	Symmetry, 2, 1.29% Symmetry 2 publications, 1.29%
Pharmaceuticals	Pharmaceuticals, 2, 1.29% Pharmaceuticals 2 publications, 1.29%
Tetrahedron Letters	Tetrahedron Letters, 2, 1.29% Tetrahedron Letters 2 publications, 1.29%
Journal of Molecular Structure	Journal of Molecular Structure, 2, 1.29% Journal of Molecular Structure 2 publications, 1.29%
Chemistry - An Asian Journal	Chemistry - An Asian Journal, 2, 1.29% Chemistry - An Asian Journal 2 publications, 1.29%
ChemBioChem	ChemBioChem, 2, 1.29% ChemBioChem 2 publications, 1.29%
Journal of the American Chemical Society	Journal of the American Chemical Society, 2, 1.29% Journal of the American Chemical Society 2 publications, 1.29%
New Journal of Chemistry	New Journal of Chemistry, 2, 1.29% New Journal of Chemistry 2 publications, 1.29%
Journal of Physical Chemistry B	Journal of Physical Chemistry B, 2, 1.29% Journal of Physical Chemistry B 2 publications, 1.29%
Dyes and Pigments	Dyes and Pigments, 1, 0.65% Dyes and Pigments 1 publication, 0.65%
	1 2 3 4 5 6 7 8

Citations by publishers

	5 10 15 20 25 30 35 40 45 50
Wiley	Wiley, 49, 31.61% Wiley 49 publications, 31.61%
Elsevier	Elsevier, 32, 20.65% Elsevier 32 publications, 20.65%
American Chemical Society (ACS)	American Chemical Society (ACS), 22, 14.19% American Chemical Society (ACS) 22 publications, 14.19%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 16, 10.32% Royal Society of Chemistry (RSC) 16 publications, 10.32%
Multidisciplinary Digital Publishing Institute (MDPI)	Multidisciplinary Digital Publishing Institute (MDPI), 16, 10.32% Multidisciplinary Digital Publishing Institute (MDPI) 16 publications, 10.32%
Springer Nature	Springer Nature, 6, 3.87% Springer Nature 6 publications, 3.87%
Beilstein-Institut	Beilstein-Institut, 3, 1.94% Beilstein-Institut 3 publications, 1.94%
Taylor & Francis	Taylor & Francis, 3, 1.94% Taylor & Francis 3 publications, 1.94%
Bentham Science	Bentham Science, 1, 0.65% Bentham Science 1 publication, 0.65%
Copernicus	Copernicus, 1, 0.65% Copernicus 1 publication, 0.65%
Shanghai Institute of Organic Chemistry	Shanghai Institute of Organic Chemistry, 1, 0.65% Shanghai Institute of Organic Chemistry 1 publication, 0.65%
Frontiers Media S.A.	Frontiers Media S.A., 1, 0.65% Frontiers Media S.A. 1 publication, 0.65%
Thieme	Thieme, 1, 0.65% Thieme 1 publication, 0.65%
	5 10 15 20 25 30 35 40 45 50

We do not take into account publications that without a DOI.
Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
Statistics recalculated weekly.

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Mei H. et al. Applications of fluorine-containing amino acids for drug design // European Journal of Medicinal Chemistry. 2020. Vol. 186. p. 111826.

GOST all authors (up to 50) Copy

Mei H., Han J., Klika K. D., Izawa K., SATO T., Meanwell N. A., Soloshonok V. A. Applications of fluorine-containing amino acids for drug design // European Journal of Medicinal Chemistry. 2020. Vol. 186. p. 111826.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1016/j.ejmech.2019.111826

UR - https://doi.org/10.1016/j.ejmech.2019.111826

TI - Applications of fluorine-containing amino acids for drug design

T2 - European Journal of Medicinal Chemistry

AU - Mei, Haibo

AU - Han, Jianlin

AU - Klika, Karel D.

AU - Izawa, Kunisuke

AU - SATO, Tatsunori

AU - Meanwell, Nicholas A.

AU - Soloshonok, Vadim A.

PY - 2020

DA - 2020/01/01 00:00:00

PB - Elsevier

SP - 111826

VL - 186

SN - 0223-5234

SN - 1768-3254

ER -

BibTex

Cite this

BibTex Copy

@article{2020_Mei,

author = {Haibo Mei and Jianlin Han and Karel D. Klika and Kunisuke Izawa and Tatsunori SATO and Nicholas A. Meanwell and Vadim A. Soloshonok},

title = {Applications of fluorine-containing amino acids for drug design},

journal = {European Journal of Medicinal Chemistry},

year = {2020},

volume = {186},

publisher = {Elsevier},

month = {jan},

url = {https://doi.org/10.1016/j.ejmech.2019.111826},

pages = {111826},

doi = {10.1016/j.ejmech.2019.111826}

}

Found error?

Publisher

Elsevier

Journal

European Journal of Medicinal Chemistry

Quartile SCImago

Quartile WOS

Impact factor

6.7

ISSN

02235234 (Print)
17683254 (Electronic)