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

Chemistry of Heterocyclic Compounds 2015
Jevgeņija Lugiņina, Ērika Bizdēna, Ainars Leonciks, Viktors Kumpiņš, Inguna Grīnšteine, Māris Turks

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.

Keywords
milbemycin A3, milbemycin A4, antibacterial activity, Staphylococcus aureus, Staphylococcus epidermidis
DOI
10.1007/s10593-014-1604-2
Hyperlink
http://link.springer.com/article/10.1007%2Fs10593-014-1604-2

Lugiņina, J., Bizdēna, Ē., Leonciks, A., Kumpiņš, V., Grīnšteine, I., Turks, M. Synthesis and Antibacterial Activity of 5-Phthalate and 5-Glutarate Derivatives of Milbemycins A3/A4*. Chemistry of Heterocyclic Compounds, 2015, Vol.50, Iss.10, pp.1404-1412. ISSN 0009-3122. e-ISSN 1573-8353. Available from: doi:10.1007/s10593-014-1604-2

Publication language
English (en)