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Articles

Thiacalix[4]arene phosphoric acids. Synthesis, structure, and inhibition of glutathione S-transferases

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Pages 538-541 | Received 12 Oct 2021, Accepted 20 Nov 2021, Published online: 17 Dec 2021

References

  • Gutsche, C. Calixarenes Revisited; Cambridge: The Royal Society of Chemistry, 1998.
  • Neri P., Sessler J. L., Wang M.-X., Eds. Calixarenes and Beyond; Springer: Switzerland, 2016.
  • Giuliani, M.; Morbioli, I.; Sansone, F.; Casnati, A. Moulding Calixarenes for Biomacromolecule Targeting. Chem. Commun (Camb)). 2015, 51, 14140–14159. DOI: 10.1039/c5cc05204a.
  • Pan, Y.-C.; Hu, X.-Y.; Guo, D.-S. Biomedical Applications of Calixarenes: state of the Art and Perspectives. Angew. Chem. Int. Ed. Engl. 2021, 60, 2768–2794. DOI: 10.1002/anie.201916380.
  • Trush, V. V.; Cherenok, S. O.; Tanchuk, V.; Yu, Kukhar, V. P.; Kalchenko, V. I.; Vovk, A. I. Calix[4]Arene Methylenebisphosphonic Acids as Inhibitors of Protein Tyrosine Phosphatase 1B. Bioorg. Med. Chem. Lett. 2013, 23, 5619–5623.
  • Vovk, A. I.; Tanchuk, V.; Yu, Kononets, L. A.; Cherenok, S. O.; Drapailo, A. B.; Kalchenko, V. I.; Kukhar, V. P. A Novel Approach to the Design of Phosphonate Inhibitors of Protein Tyrosine Phosphatase. Phosphorus Sulfur Silicon Relat. Elem. 2011, 186, 958–960. DOI: 10.1080/10426507.2010.521213.
  • Vovk, A. I.; Kononets, L. A.; Tanchuk, V.; Yu, Cherenok, S. O.; Drapailo, A. B.; Kalchenko, V. I.; Kukhar, V. P. Inhibition of Yersinia Protein Tyrosine Phosphatase by Phosphonate Derivatives of Calixarenes. Bioorg. Med. Chem. Lett. 2010, 20, 483–487.
  • Vovk, A. I.; Kononets, L. A.; Tanchuk, V. Y.; Drapailo, A. B.; Kalchenko, V. I.; Kukhar, V. P. Thiacalix [4] Arene as Molecular Platform for Design of Alkaline Phosphatase Inhibitors. J. Incl. Phenom. Macrocycl. Chem. 2010, 66, 271–277. DOI: 10.1007/s10847-009-9607-9.
  • Cherenok, S. O.; Yushchenko, O. A.; Tanchuk, V.; Yu, Mischenko, I. M.; Samus, N. V.; Ruban, O. V.; Matvieiev, Y. I.; Karpenko, J. A.; Kukhar, V. P.; Vovk, A. I.; et al. Calix[4]Arene-α-Hydroxyphosphonic Acids. Synthesis, Stereochemistry, and Inhibition of Glutathione S-Transferase. Arkivoc 2012, 2012, 278–298. DOI: 10.3998/ark.5550190.0013.421.
  • Vovk, A. I.; Mischenko, I. M.; Cherenok, S. O.; Tanchuk, V.; Yu, Kalchenko, V. I.; Kukhar, V. P. Phosphorylated Calix[4]Arenes as Inhibitors of Glutathione S-Transferase. Phosphorus, Sulfur Silicon Relat. Elem. 2011, 186, 961–963. DOI: 10.1080/10426507.2010.514313.
  • Trush, V. V.; Kharchenko, S. G.; Tanchuk, V.; Yu, Kalchenko, V. I.; Vovk, A. I. Phosphonate Monoesters on a Thiacalix[4]Arene Framework as Potential Inhibitors of Protein Tyrosine Phosphatase 1B. Org. Biomol. Chem. 2015, 13, 8803–8806. DOI: 10.1039/C5OB01247C.
  • Humbert, N.; Kovalenko, L.; Saladini, F.; Giannini, A.; Pires, M.; Botzanowski, T.; Cherenok, S.; Boudier, C.; Sharma, K. K.; Real, E.; et al. ( Thia)Calixarenephosphonic Acids as Potent Inhibitors of the Nucleic Acid Chaperone Activity of the HIV-1 Nucleocapsid Protein with a New Binding Mode and Multitarget Antiviral Activity. ACS Infect. Dis. 2020, 6, 687–702.
  • McKenna, C. E.; Higa, M. T.; Cheung, N. H.; McKenna, M.-C. The Facile Dealkylation of Phosphonic Acid Dialkyl Esters by Bromotrimethylsilane. Tetrahedron Lett. 1977, 18, 155–158. DOI: 10.1016/S0040-4039(01)92575-4.
  • Sevrain, C. M.; Berchel, M.; Couthon, H.; Jaffrès, P. A. Phosphonic Acid: preparation and Applications. Beilstein J. Org. Chem. 2017, 13, 2186–2213. DOI: 10.3762/bjoc.13.219.
  • Hanna, P. E.; Anders, M. W. The Mercapturic Acid Pathway. Crit. Rev. Toxicol. 2019, 49, 819–929. DOI: 10.1080/10408444.2019.1692191.

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