ChemMedChem, volume 13, issue 19, pages 2080-2089
Synthesis, Structural Characterization, and Antiangiogenic Activity of Polyfluorinated Benzamides
Christian Steinebach
1
,
Agnieszka Ambrożak
1
,
Stefan Dosa
1
,
Shaunna L. Beedie
2
,
Jonathan D. Strope
2
,
Gregor Schnakenburg
3
,
William D Figg
2
,
2
Molecular Pharmacology Section; National Cancer Institute, NIH; Bethesda MD 20892 USA
|
Publication type: Journal Article
Publication date: 2018-09-06
Journal:
ChemMedChem
Quartile SCImago
Q1
Quartile WOS
Q2
Impact factor: 3.4
ISSN: 18607179, 18607187
Organic Chemistry
Drug Discovery
Biochemistry
Pharmacology
Molecular Medicine
General Pharmacology, Toxicology and Pharmaceutics
Abstract
The introduction of fluorine into bioactive molecules is a matter of importance in medicinal chemistry. In this study, representatives of various chemical entities of fluoroaromatic compounds were synthesized. Depending on the reaction conditions, either tetrafluorophthalimides or ammonium tetrafluorophthalamates are accessible from tetrafluorophthalic anhydride and primary amines. Tetrafluorophthalamic acids undergo thermal decarboxylation to yield tetrafluorobenzamides. These could be successfully converted upon treatment with primary amines, in the course of an aromatic nucleophilic substitution, to 2,3,5-trifluorobenzamides with respective amino substituents at the 4-position. The five structure types were characterized by means of spectroscopic and crystallographic methods. The synthesized compounds were evaluated as inhibitors of angiogenesis by measuring microvessel outgrowth in a rat aortic ring assay. The biological activity was maintained throughout these different polyfluorinated chemotypes.
Top-30
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1 publication, 12.5%
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1 publication, 12.5%
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Citations by publishers
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1
2
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Multidisciplinary Digital Publishing Institute (MDPI)
2 publications, 25%
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Elsevier
2 publications, 25%
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Springer Nature
1 publication, 12.5%
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Wiley
1 publication, 12.5%
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American Chemical Society (ACS)
1 publication, 12.5%
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 12.5%
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- We do not take into account publications 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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Steinebach C. et al. Synthesis, Structural Characterization, and Antiangiogenic Activity of Polyfluorinated Benzamides // ChemMedChem. 2018. Vol. 13. No. 19. pp. 2080-2089.
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Steinebach C., Ambrożak A., Dosa S., Beedie S. L., Strope J. D., Schnakenburg G., Figg W. D., Gütschow M. Synthesis, Structural Characterization, and Antiangiogenic Activity of Polyfluorinated Benzamides // ChemMedChem. 2018. Vol. 13. No. 19. pp. 2080-2089.
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TY - JOUR
DO - 10.1002/cmdc.201800263
UR - https://doi.org/10.1002/cmdc.201800263
TI - Synthesis, Structural Characterization, and Antiangiogenic Activity of Polyfluorinated Benzamides
T2 - ChemMedChem
AU - Ambrożak, Agnieszka
AU - Dosa, Stefan
AU - Beedie, Shaunna L.
AU - Strope, Jonathan D.
AU - Gütschow, Michael
AU - Steinebach, Christian
AU - Schnakenburg, Gregor
AU - Figg, William D
PY - 2018
DA - 2018/09/06 00:00:00
PB - Wiley
SP - 2080-2089
IS - 19
VL - 13
SN - 1860-7179
SN - 1860-7187
ER -
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@article{2018_Steinebach,
author = {Agnieszka Ambrożak and Stefan Dosa and Shaunna L. Beedie and Jonathan D. Strope and Michael Gütschow and Christian Steinebach and Gregor Schnakenburg and William D Figg},
title = {Synthesis, Structural Characterization, and Antiangiogenic Activity of Polyfluorinated Benzamides},
journal = {ChemMedChem},
year = {2018},
volume = {13},
publisher = {Wiley},
month = {sep},
url = {https://doi.org/10.1002/cmdc.201800263},
number = {19},
pages = {2080--2089},
doi = {10.1002/cmdc.201800263}
}
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Steinebach, Christian, et al. “Synthesis, Structural Characterization, and Antiangiogenic Activity of Polyfluorinated Benzamides.” ChemMedChem, vol. 13, no. 19, Sep. 2018, pp. 2080-2089. https://doi.org/10.1002/cmdc.201800263.