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New crystal structures of fluorinated α-aminophosphonic acid analogues of phenylglycine

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Abstract

The four novel phosphonic acid analogues of phenylglycine with various substituents in phenyl ring (mostly fluorine atoms) have been synthesized by using procedure of amidoalkylation of phosphorus trichloride with aromatic aldehydes and acetamide. The NMR, ESI-MS spectroscopy, and single-crystal X-Ray diffraction methods were used to characterize unusual structures: the amino-(4-trifluoromethylbenzyl)-(1), amino-(3,4-difluorobenzyl)-(2), amino-(2,4,6-trifluorobenzyl)-(3), and amino-(2-fluoro-4-hydroxybenzyl)-(4) phosphonic acids. Since the α-aminophosphonates have a potential for biological activity and could be used as building blocks in medicinal chemistry, it is important to know their detail crystal structures and properties which, in turn, may extend the knowledge on their interaction with physiologic receptors.

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  • 27 February 2020

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Funding

This work was supported by Narodowe Centrum Nauki, grant number 2017/26/M/ST5/00437.

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Authors and Affiliations

  1. Faculty of Chemistry, Wroclaw University of Science and Technology, Wybrzeze Wyspianskiego 27, 50-370, Wroclaw, Poland

    Weronika Wanat, Błażej Dziuk & Paweł Kafarski

  2. Faculty of Chemistry, University of Opole, Opole, ul. Oleska 48, 45-052, Opole, Poland

    Błażej Dziuk

Authors
  1. Weronika Wanat
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  2. Błażej Dziuk
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  3. Paweł Kafarski
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Correspondence to Weronika Wanat.

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Wanat, W., Dziuk, B. & Kafarski, P. New crystal structures of fluorinated α-aminophosphonic acid analogues of phenylglycine. Struct Chem 31, 1197–1209 (2020). https://doi.org/10.1007/s11224-019-01483-x

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