Struct Chem
14. Lejczak B, Kafarski P (2009) Biological Activity of
Aminophosphonic Acids and Their Short Peptides. Top
Heterocycl Chem 20:31–63
15. Wang J, Sanchez-Rosello M, Acena C, del Pozo JL, Sorochinsky
AE, Fustero S, Soloshonok VA, Liu H (2014) Fluorine in pharma-
ceutical industry: fluorine-containing drugs introduced to the mar-
ket in the last decade (2001–2011). Chem Rev 114:2432–2506
16. O’Hagan D, Rzepa HS (1997) Some influences of fluorine in
bioorganic chemistry. Chem Commun 7:645–652
different direction forming variety of supramolecular
synthons. Hirshfeld surface analysis reveals that O/H and H/
H contacts dominate over all the atom-atom contacts. The
presence of one or several fluorine atoms expands the network
of F···H interaction and along with the absence of N···N con-
tacts in the molecule confirms the main role of C-H···N
interaction.
17. LeVine H (1999) Quantification of beta-sheet amyloid fibril struc-
tures with thioflavin T. Methods Enzymol 309:274–284
18. Lemal DM (2004) Perspective on Fluorocarbon Chemistry. J Org
Chem 69:1–11
Funding information This work was supported by Narodowe Centrum
Nauki, grant number 2017/26/M/ST5/00437.
19. Ojima I (2009) Fluorine in Medicinal Chemistry and Chemical
Biology, New York
Compliance with ethical standards
20. Minks C, Huber R, Moroder L, Budisa N (2000) Noninvasive trac-
ing of recombinant proteins with “fluorophenylalanine-fingers”.
Anal Biochem 284:29–34
Conflict of interest The authors declare that they have no conflict of
interest.
21. Wanat W, Talma M, Hurek J, Pawełczak M, Kafarski P (2018)
Substituted phosphonic analogues of phenylglycine as inhibitors
of phenylalanine ammonia lyase from potatoes. Biochimie 115:
119–127
References
22. Oleksyszyn J, Soroka M, Rachoń J (1978) Phosphorus analogs of
amino-acids and pepetides. 2. Phosphoanalogs and
phosphinanalogs of cycloleucin. Chimia 32:253–255
23. Oleksyszyn J, Tyka R, Mastalerz P (1978) Direct synthesis of 1-
aminoalkanephosphonic and 1- aminoalkanephosphinic acids from
phosphorus trichloride or dichlorophosphines. Synthesis:479–480
24. Soroka M (1989) Comments on the synthesis of
aminomethylphosphonic acid. Synthesis:547–548
25. CrysAlis CCD (2002) Oxford Diffraction Ltd.: Abingdon, England,
CrysAlis RED (2002) Oxford Diffraction Ltd.: Abingdon, England
26. Sheldrick GM (2008) A short history of SHELX. Acta Crystallogr
A 64:112–122
27. Sheldrick GM (2015) Crystal structure refinement with SHELXL.
Acta Crystallogr Sect C 71:3–8
28. Macrae CF, Bruno IJ, Chisholm JA, Edgington PR, McCabe P,
Pidcock E, Rodriguez-Monge L, Taylor R, van de Streek J, Wood
PA (2008) New Features for the Visualization and Investigation of
Crystal Structures. J Appl Crystallogr 41:466–470
2 9 . Sawka-Dobrowolska W (1985) St ructure of α-
(Isopropylamino)salicylphosphonic Acid Hemihydrate,
C10H16NO4P.0.5H2O. Acta Crystallogr Sect C 41:84–86
30. Sawka-Dobrowolska W (1988) Structure of (R), 1-[(R)-1-
Phenylethylamino]benzylphosphonic Acid Sesquihydrate. Acta
Crystallogr Sect C 44:1624–1627
1. Mastalerz P (1959). Arch Immun Ter Dośw 2:201–210
2. Mastalerz P (1960). Chem Abstr 54:6843
3. Mucha A, Kafarski P, Berlicki Ł (2011) Remarkable potential of the
α-aminophosphonate/phosphinate structural motif in medicinal
chemistry. J Med Chem 54:5955–5980
4. Mucha A (2012) Synthesis and Modifications of Phosphinic
Dipeptide Analogues. Molecules 17:13530–13,568
5. Węglarz-Tomczak E, Vassiliou S, Mucha A (2016) Discovery of
potent and selective inhibitors of human aminopeptidases ERAP1
and ERAP2 by screening libraries of phosphorus-containing amino
acid and dipeptide analogues. Bioorg Med Chem Lett 26:4122–
4126
6. Fang YL, Wu ZL, Xiao MW, Tang YT, Li KM, Ye J, Xiang JN, Hu
AX (2016) One-Pot Three-Component Synthesis of Novel Diethyl((2-
oxo-1,2-dihydroquinolin-3-yl)(arylamino)methyl)phosphonate as
Potential Anticancer Agents. Int J Mol Sci 17:653–667
7. Bhattacharya AK, Raut DS, Rana KC, Polanki IK, Khan MS, Iram
S (2013) Diversity-oriented synthesis of α-aminophosphonates: a
new class of potential anticancer agents. Eur J Med Chem 66:146–
152
8. Dake SA, Raut DS, Kharat KR, Mhaske RS, Deshmukh SU, Pawar
RP (2011) Ionic liquid promoted synthesis, antibacterial and in vitro
antiproliferative activity of novel α-aminophosphonate derivatives.
Bioorg Med Chem Lett 21:2527–2532
31. Nazir H, Yilmaz H, Tahir MN, Ülkü D (1999) Synthesis of
Substituted α-N-(2-Hydroxyethyl)- Aminomethylphosphonic
Acid Monoethylester Derivatives. Synth React In Met-Org Chem
29(10):1821–1828
32. Sowa M, Ślepokura K, Goldeman W, Duczmal M, Wojciechowska
A, Matczak-Jon E (2013) Structural characterization of pyridin-2-,
9. Hellal A, Chafaa S, Chafai N, Touafri L (2017) Synthesis, antibac-
terial screening and DFTstudies of series of α-amino-phosphonates
derivatives from aminophenols. J Mol Struct 1134:217–225
10. Lan X, Xie D, Yin L, Wang Z, Chen J, Zhang A, Song B, Hu D
(2017) Novel α,β-unsaturated amide derivatives bearing α-amino
phosphonate moiety as potential antiviral agents. Bioorg Med
Chem Lett 27:4270–4273
− 3 - ,
a n d − 4 - y l
f u n c t i o n a l i z e d
(iminodimethanediyl)bis(phosphonic) acids: Insight into the
cobalt(II) and copper(II) complexes of pyridin-2-yl derivative.
Polyhedron 50:398–409
11. Romero-Estudillo I, Viveros-Ceballos JL, Cazares-Carreño O,
González-Morales A, Flores de Jesús B, López-Castillo M, Razo-
Hernández RS, Castañeda-Corral G, Ordóñez M (2018) Synthesis
of new α-aminophosphonates: Evaluation as anti-inflammatory
agents and QSAR studies. Bioorg Med Chem 15:2376–2386
12. Qin Y, Xing R, Liu S, Yu H, Li K, Hu L, Li P (2014) Synthesis and
antifungal properties of (4-tolyloxy)-pyrimidyl-α-
aminophosphonates chitosan derivatives. Int J Biol Macromol 63:
83–91
33. Hua F, Meijuan F, Xiaoxia L, Guo T, Yufen Z (2007) Syntheses,
Characterizations, and Crystal Structures of Phosphonopeptides.
Heteroat Chem 18:9–15
34. Naydenova ED, Todorov PT, Troev KD (2010) Recent synthesis of
aminophosphonic acids as potential biological importance. Amino
Acids 38:23–30
13. Kafarski P, Lejczak B (2001) Aminophosphonic Acids of Potential
Medical Importance. Curr Med Chem Anticancer Agents 1:301–
312
35. Visnjevac A, Tusek-Bozic L (2004) Two types of monoethyl a-
anilino-benzylphosphonates: a zwitterion and a molecular com-
pound. Acta Crystallogr Sect C 60:434–437