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Russian Journal of Organic Chemistry

, Volume 55, Issue 6, pp 755–761 | Cite as

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

  • V. P. KrasnovEmail author
  • A. Yu. Vigorov
  • E. N. Chulakov
  • I. A. Nizova
  • G. L. Levit
  • M. A. Kravchenko
  • V. N. Charushin
Article
  • 13 Downloads

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.

Keywords

purines conjugates 4-aminobenzoic acid glutamic acid tuberculostatic activity 

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Notes

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).

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Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • V. P. Krasnov
    • 1
    Email author
  • A. Yu. Vigorov
    • 1
  • E. N. Chulakov
    • 1
  • I. A. Nizova
    • 1
  • G. L. Levit
    • 1
  • M. A. Kravchenko
    • 2
  • V. N. Charushin
    • 1
    • 3
  1. 1.Postovskii Institute of Organic Synthesis, Ural BranchRussian Academy of SciencesYekaterinburgRussia
  2. 2.Ural Research Institute of PhthisiopulmonologyNational Medical Research Center, Ministry of Healthcare of the Russian FederationYekaterinburgRussia
  3. 3.Institute of Chemical EngineeringYeltsin Ural Federal UniversityYekaterinburgRussia

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