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Synthesis of Purine and 2-Aminopurine Conjugates with N-(4-Aminobenzoyl)-(S)-glutamic Acid

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Abstract

Purine and 2-aminopurine conjugates with N-(4-aminobenzoyl)-(S)-glutamic acid connected to C6 of the purine system either directly or through an aminoethyl linker have been synthesized by nucleophilic substitution of chlorine in 6-chloropurine and 2-amino-6-chloropurine. 2-Aminopurine conjugate with 4-aminobenzoic acid linked through a glycine residue has also been obtained. Testing of the synthesized compounds for tuberculostatic activity in vitro has revealed a moderate activity of methyl 4-[2-(2-aminopurin-6-ylamino)-acetyl]amino}benzoate.

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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, and the Group of Elemental Analysis under the guidance of Dr. L.N. Bazhenova (Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences). This study was performed 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).

Author information

Authors and Affiliations

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

    V. P. Krasnov, A. Yu. Vigorov, E. N. Chulakov, I. A. Nizova, G. L. Levit & V. N. Charushin

  2. Ural Research Institute of Phthisiopulmonology, National Medical Research Center, Ministry of Healthcare of the Russian Federation, Yekaterinburg, Russia

    M. A. Kravchenko

  3. Institute of Chemical Engineering, Yeltsin Ural Federal University, Yekaterinburg, Russia

    V. N. Charushin

Authors
  1. V. P. Krasnov
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  2. A. Yu. Vigorov
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  3. E. N. Chulakov
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  4. I. A. Nizova
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  5. G. L. Levit
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  6. M. A. Kravchenko
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  7. 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. 848–855.

Conflict of Interests

The authors declare the absence of conflict of interests.

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Krasnov, V.P., Vigorov, A.Y., Chulakov, E.N. et al. Synthesis of Purine and 2-Aminopurine Conjugates with N-(4-Aminobenzoyl)-(S)-glutamic Acid. Russ J Org Chem 55, 755–761 (2019). https://doi.org/10.1134/S1070428019060034

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  • DOI: https://doi.org/10.1134/S1070428019060034

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