Chemistry of Heterocyclic Compounds

, Volume 50, Issue 10, pp 1404–1412 | Cite as

Synthesis and Antibacterial Activity of 5-Phthalate and 5-Glutarate Derivatives of Milbemycins A3/A4*

  • J. Lugiņina
  • Ē. Bizdēna
  • A. Leonciks
  • V. Kumpiņš
  • I. Grīnšteine
  • M. TurksEmail author

Naturally occurring 16-membered macrolides milbemycins A3 and A4 were selectively esterified at their 5-OH group with phthalic and glutaric anhydrides. The obtained monoesters were further functionalized by amide formation. Propargylamide derivatives were demonstrated to undergo 1,2,3-triazole formation upon treatment with organic azides in the presence of copper catalyst. Some of the synthesized compounds exhibited useful levels of antibacterial properties against Staphylococcus aureus and Staphylococcus epidermidis.


milbemycin A3 milbemycin A4 antibacterial activity Staphylococcus aureus Staphylococcus epidermidis 


This work was supported by the ERDF project 2DP/

Supplementary material

10593_2014_1604_MOESM1_ESM.pdf (5.9 mb)
ESM 1 The Supplementary file containing experimental and HPLC data, as well as 1H and 13C NMR spectra of compounds 211 a,b, is available to authorized users. (PDF 6053 kb)


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Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • J. Lugiņina
    • 1
  • Ē. Bizdēna
    • 1
  • A. Leonciks
    • 2
  • V. Kumpiņš
    • 1
  • I. Grīnšteine
    • 1
    • 3
  • M. Turks
    • 1
    Email author
  1. 1.Riga Technical UniversityRigaLatvia
  2. 2.Latvian Biomedical Research and Study CenterRigaLatvia
  3. 3.PharmIdea Ltd.OlaineLatvia

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