Synthesis and cytotoxicity of aminoethoxydiphenyls

Authors

  • S. O. Zanoza Physical-Chemical Institute O.V. Bogatsky National Academy of Sciences of Ukraine, Ukraine
  • G. V. Maltzev Physical-Chemical Institute O.V. Bogatsky National Academy of Sciences of Ukraine, Ukraine
  • S. A. Lyakhov Physical-Chemical Institute O.V. Bogatsky National Academy of Sciences of Ukraine, Ukraine
  • S. A. Andronati Physical-Chemical Institute O.V. Bogatsky National Academy of Sciences of Ukraine, Ukraine
  • M. Yu. Zubritskiy Institute of Physical-Organic Chemistry and Coal Chemistry them. L.M. Lytvynenko National Academy of Sciences of Ukraine, Ukraine
  • O. S. Bogorad-Kobelska Institute of Microbiology and Virology them. D.K. Zabolotniy of the National Academy of Sciences of Ukraine, Ukraine
  • O. V. Plotka Institute of Microbiology and Virology them. D.K. Zabolotniy of the National Academy of Sciences of Ukraine, Ukraine
  • N. M. Zholobak Institute of Microbiology and Virology them. D.K. Zabolotniy of the National Academy of Sciences of Ukraine, Ukraine
  • M. Ya. Spivak Institute of Microbiology and Virology them. D.K. Zabolotniy of the National Academy of Sciences of Ukraine, Ukraine

DOI:

https://doi.org/10.24959/ophcj.14.807

Keywords:

diaminoethoxydiphenyls, antiviral drugs, cytotoxicity

Abstract

The implementation mechanism of the antiviral activity (AA) and interferon induction (IFI) by planar polycyclic compounds has not yet been determined. However, our hypothesis of the priority role of intercalation in double strand nucleic acids (NA) has gained strong arguments in its favour in our works and the works of foreign colleagues.
On the other hand, the presence of AA and the ability to induce IFI in biphenyl derivatives that are incapable to intercalate in NA indicates the possibility of implementing alternative mechanisms. This determined our interest to the study of aminoethoxydiphenyls (AED), which synthesis and investigation of cytotoxicity become the subject of this article. 4,4’-Bis-(2-chloroethoxy)diphenyl was obtained by alkylation of dihydroxydiphenyl with dichloroethane in its mixture with aqueous sodium hydroxide (20%) in the presence of tetrabutylammonium chloride (TBAC). Series of AED were synthesized by substitution of chlorine by iodine in the mixture of xylene with the aqueous solution of sodium iodide in the presence of TBAC with subsequent amination with primary and secondary amines. The protonated molecular ions (MI) intensive peaks of the compounds synthesized are observed in the mass spectra with FAB ionization. The most common way of MI fragmentation is PhO-CH2-bond cleavage following the side aminoalkyl fragment detachment. Absorption bands typical for CH (arom.), CH (aliph.), COC bonds and NH protonated terminal amino groups are present in IR spectra. In the 1H-NMR spectra signals from aromatic and aliphatic protons present, multiplicity and integral intensity correspond to the attributed structures. Cytotoxicity of the compounds synthesized was tested using EPT cells in vitro. All AED tested appeared to be comparable to amixine and are in the range from low to moderate cytotoxicity.

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Published

2014-09-12

How to Cite

(1)
Zanoza, S. O.; Maltzev, G. V.; Lyakhov, S. A.; Andronati, S. A.; Zubritskiy, M. Y.; Bogorad-Kobelska, O. S.; Plotka, O. V.; Zholobak, N. M.; Spivak, M. Y. Synthesis and Cytotoxicity of Aminoethoxydiphenyls. J. Org. Pharm. Chem. 2014, 12, 38-44.

Issue

Vol. 12 No. 3(47) (2014)

Section

Original Researches

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