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Synthesis of New Purine Derivatives Containing α- and ω-Amino Acid Fragments

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Abstract

New conjugates of purine and 2-aminopurine with several α- and ω-amino acids have been synthesized following two approaches based on the condensation and nucleophilic substitution reactions. The enantiomeric purity of the isolated compounds has been confirmed by reversed-phase HPLC using a chiral stationary phase to demonstrate the absence of racemization during the synthesis. The conjugates are inactive against Mycobacterium tuberculosis H37Rv.

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Acknowledgments

The authors thank Dr. M.I. Kodess and M.A. Ezhikova for recording the NMR spectra, Dr. I.N. Ganebnykh for recording the high-resolution mass spectra, the Group of Elemental Analysis under the guidance of Dr. L.N. Bazhenova (Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences), Dr. A.A. Tumashov for performing HPLC analyses, and Dr. M.A. Kravchenko for performing in vitro biological studies. This study was carried out using the equipment of the “Spectroscopy and Analysis of Organic Compounds” joint center.

Funding

This study was performed under financial support by the Russian Science Foundation (project no. 19-13-00231).

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Authors and Affiliations

  1. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, Yekaterinburg, Russia

    V. V. Musiyak, I. A. Nizova, T. V. Matveeva, G. L. Levit, V. P. Krasnov & V. N. Charushin

Authors
  1. V. V. Musiyak
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  2. I. A. Nizova
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  3. T. V. Matveeva
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  4. G. L. Levit
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  5. V. P. Krasnov
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  6. V. N. Charushin
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Corresponding author

Correspondence to V. P. Krasnov.

Additional information

Dedicated to Full Member of the Russian Academy of Sciences O.N. Chupakhin on his 85th anniversary

Russian Text© The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 6, pp. 856–865.

Conflict of Interests

The authors declare the absence of conflict of interests.

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Musiyak, V.V., Nizova, I.A., Matveeva, T.V. et al. Synthesis of New Purine Derivatives Containing α- and ω-Amino Acid Fragments. Russ J Org Chem 55, 762–770 (2019). https://doi.org/10.1134/S1070428019060046

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  • DOI: https://doi.org/10.1134/S1070428019060046

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