These authors contributed equally in this work.
Effect of 3-Alkylpyridine Marine Alkaloid Analogues in Leishmania Species Related to American Cutaneous Leishmaniasis
Article first published online: 10 SEP 2012
© 2012 John Wiley & Sons A/S
Chemical Biology & Drug Design
Volume 80, Issue 5, pages 745–751, November 2012
How to Cite
Machado, P. A., Hilário, F. F., Carvalho, L. O., Silveira, M. L. T., Alves, R. B., Freitas, R. P. and Coimbra, E. S. (2012), Effect of 3-Alkylpyridine Marine Alkaloid Analogues in Leishmania Species Related to American Cutaneous Leishmaniasis. Chemical Biology & Drug Design, 80: 745–751. doi: 10.1111/cbdd.12017
- Issue published online: 5 OCT 2012
- Article first published online: 10 SEP 2012
- Accepted manuscript online: 8 AUG 2012 09:42AM EST
- Received 28 December 2011, revised 18 July 2012 and accepted for publication 2 August 2012
- 3-alkylpyridine alkaloids;
- marine alkaloids
A series of oxygenated analogues of marine 3-alkylpyridine alkaloids were synthesized, and their leishmanicidal activity was assayed. All compounds were prepared from 3-pyridinepropanol in few steps and in good yields. The key step for the synthesis of these compounds was a classic Williamson etherification under phase-transfer conditions. Besides toxicity in peritoneal macrophages, the compounds exhibited a significant leishmanicidal activity. Of twelve compounds tested, five showed a strong leishmanicidal activity against promastigote forms of Leishmania amazonensis and L. braziliensis with IC50 below 10 μm. Compounds 11, 14, 15, and 16 showed a strong leishmanicidal activity on intracellular amastigotes (IC50 values of 2.78; 0.27; 1.03, and 1.33 μm, respectively), which is unlikely to be owing to the activation of nitric oxide production by macrophages.