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Synthesis, Crystal Structure, and Biological Activity of α-Hydroxyphosphonates

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Abstract

A series of dialkyl [aryl(hydroxy)methyl]phosphonates with various substituents at the phosphorus atom was obtained by the Abramov reaction. The structure of the isolated products was confirmed by IR and NMR spectroscopy, mass spectrometry, and X-ray diffraction analysis. All the obtained compounds demonstrated activity against B. cereus and S. aureus bacterial strains.

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CONFLICT OF INTEREST

The authors declare no conflict of interest.

REFERENCES

  1. Tezel, U. and Pavlostathis, S.G., Curr. Opin. Biotechnol., 2015, vol. 33, p. 296. https://doi.org/10.1016/j.copbio.2015.03.018

    Article  CAS  PubMed  Google Scholar 

  2. Buffet-Bataillona, S., Tattevinc, P., Bonnaure-Mallet, M., and Jolivet-Gougeonb, A., Int. J. Antimicrob. Agents, 2012, vol. 39, p. 381. https://doi.org/10.1016/j.ijantimicag.2012.01.011

    Article  CAS  Google Scholar 

  3. Pateiro-Moure, M., Arias-Estevez, M., and Simal-Gandara, J., Environ. Sci. Technol., 2013, vol. 47, p. 4984. https://doi.org/10.1021/es400755h

    Article  CAS  PubMed  Google Scholar 

  4. Galkina, I.V., Khayarov, K.R., Davletshin, R.R., Gaynullin, A.Z., Gerasimov, A.V., Shulaeva, M.P., Pozdeev, O.K., Egorova, S.N., Usupova, L.M., and Galkin, V.I., Phosphorus, Sulfur Silicon Relat. Elem., 2019, vol. 194, p. 463. https://doi.org/10.1080/10426507.2018.1539848

    Article  CAS  Google Scholar 

  5. Gayneev, A., Davletshin, R., Davletshina, N., Galkina, I., Mirkhuzina, M., Sedov, A., Kuchaev, E., and Islamov, D., Phosphorus, Sulfur Silicon Relat. Elem., 2022, vol. 197, p. 1. https://doi.org/10.1080/10426507.2021.2021527

    Article  CAS  Google Scholar 

  6. Davletshin, R., Gayneev, A., Ermakova, E., Davletshina, N., Galkina, I., Ivshin, K., Shulaeva, M., and Pozdeev, O., Mendeleev Commun., 2022, vol. 32, p. 180. https://doi.org/10.1016/j.mencom.2022.03.009

    Article  CAS  Google Scholar 

  7. Lima, Y.R., Da, Costa, G.P., Xavier, M.C.D.F., De Moraes, M.C., Barcellos, T., Alves, D., and Silva, M.S., ChemistrySelect, 2020, vol. 5, p. 12487. https://doi.org/10.1002/slct.202003761

    Article  CAS  Google Scholar 

  8. Kiss, N.Z., Radai, Z., and Keglevich, G., Phosphorus, Sulfur Silicon Relat. Elem., 2019, vol. 194, p. 1. https://doi.org/10.1080/10426507.2019.1630407

    Article  CAS  Google Scholar 

  9. Sampath, S., Raju, C.N., and Rao, C.V., Phosphorus, Sulfur Silicon Relat. Elem., 2016, vol. 191, p. 95. https://doi.org/10.1080/10426507.2015.1032412

    Article  CAS  Google Scholar 

  10. Kalla, R.M.N., Lee, H.R., Cao, J., Yoo, J.W., and Kim, I., New J. Chem., 2015, vol. 39, p. 3916. https://doi.org/10.1039/C4NJ01695E

    Article  CAS  Google Scholar 

  11. Kolodiazhnyi, O.I., Russ. Chem. Rev., 2006, vol. 75, p. 227. https://doi.org/10.1070/RC2006v075n03ABEH001193

    Article  CAS  Google Scholar 

  12. Prechelmacher, S., Mereiter, K., and Hammerschmidt, F., Org. Biomol. Chem., 2018, vol. 16, p. 3672. https://doi.org/10.1039/C8OB00419F

    Article  CAS  PubMed  Google Scholar 

  13. Vincze, D.A., Abranyi-Balogh, P., Bagi, P., and Keglevich, G., Molecules, 2019, vol. 24, p. 3859. https://doi.org/10.3390/molecules24213859

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. Cytlak, T., Skibinska, M., Kaczmarek, P., Kazmierczak, M., Rapp, M., Kubickia, M., and Koroniaka, H., New J. Chem., 2018, vol. 8, p. 11957. https://doi.org/10.1039/C8RA01656A

    Article  CAS  Google Scholar 

  15. Iorga, B., Eymery, F., and Savignac, P., Tetrahedron, 1999, vol. 55, p. 13109. https://doi.org/10.1016/S0040-4020(99)00822-4

    Article  Google Scholar 

  16. Baccari, Z., Sanhoury, M.A.K., Crousse, B., and Barhoumi-Slimi, T., Synth. Commun., 2018, vol. 48, p. 1. https://doi.org/10.1080/00397911.2018.1439175

    Article  CAS  Google Scholar 

  17. Desai, J., Wang, Y., Wang, K., Malwal, S.R., and Oldfield, E., ChemMedChem, 2016, vol. 11, p. 1. https://doi.org/10.1002/cmdc.201600343

    Article  CAS  Google Scholar 

  18. Zengxiang, Z., Wanhua, X., Yuxing, G., Guo, T., and Yufen, Z., Chem. Asian J., 2013, vol. 8, p. 713. https://doi.org/10.1002/asia.201201062

    Article  CAS  Google Scholar 

  19. Boobalan, R. and Chen, C., Adv. Synth. Catal., 2013, vol. 355, p. 3443. https://doi.org/10.1002/adsc.201300653

    Article  CAS  Google Scholar 

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Funding

This paper has been supported by the Kazan Federal University Strategic Academic Leadership Program (“PRIORITY-2030”).

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Authors and Affiliations

  1. Butlerov Institute of Chemistry, Kazan (Volga Region) Federal University, 420008, Kazan, Russia

    A. N. Sedov, R. R. Davletshin, N. V. Davletshina, K. A. Ivshin, A. P. Fedonin & A. R. Osogostok

  2. Kazan State Medical Academy, 420012, Kazan, Russia

    M. P. Shulaeva

Authors
  1. A. N. Sedov
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  2. R. R. Davletshin
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  3. N. V. Davletshina
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  4. K. A. Ivshin
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  5. A. P. Fedonin
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  6. A. R. Osogostok
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  7. M. P. Shulaeva
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Corresponding authors

Correspondence to A. N. Sedov or N. V. Davletshina.

Additional information

Translated from Zhurnal Organicheskoi Khimii, 2023, Vol. 59, No. 8, pp. 1065–1071 https://doi.org/10.31857/S0514749223080086.

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Sedov, A.N., Davletshin, R.R., Davletshina, N.V. et al. Synthesis, Crystal Structure, and Biological Activity of α-Hydroxyphosphonates. Russ J Org Chem 59, 1342–1347 (2023). https://doi.org/10.1134/S1070428023080080

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  • DOI: https://doi.org/10.1134/S1070428023080080

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