6533b824fe1ef96bd1280bc0

RESEARCH PRODUCT

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

Weronika WanatPaweł KafarskiBłażej DziukBłażej Dziuk

subject

010405 organic chemistryCrystal and molecular structureschemistry.chemical_elementBiological activityCrystal structure010402 general chemistryCondensed Matter PhysicsRing (chemistry)01 natural sciencesMedicinal chemistryNMRESI-MS spectra0104 chemical sciencesTurn (biochemistry)chemistry.chemical_compoundchemistryFluorinated α-aminophosphonic acidFluorinePhosphorus trichloridePhysical and Theoretical ChemistrySpectroscopyAcetamide

description

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.

https://doi.org/10.1007/s11224-019-01483-x