SYNTHESIS AND IN VITRO LEISHMANICIDAL AND CYTOTOXIC ACTIVITIES OF 2-STYRYLQUINOLINES ANALOGS

Authors

  • Ana M. MESA
  • Paula A. MOLANO M.
  • Blandine SEON
  • Bruno FIGADERE
  • Sara M. ROBLEDO
  • Diana L. MUÑOZ
  • Jairo A. SÁEZ V.

DOI:

https://doi.org/10.17533/udea.vitae.798

Keywords:

Leishmanicidal activity, 2-styrylquinolines, cytotoxicity, axenic amastigotes, intracellular

Abstract

The search of new treatments for leishmaniasis is an active task nowadays, since there is a lack of nontoxic,

cheap and non-resistant medication. In the literature several quinolines have shown in vitro activity

against agents of cutaneous leishmaniasis, visceral leishmaniasis, African trypanosomiasis and Chagas

diseases. Six 2-styrylquinolines derived from galipeine were synthesized by Perkin condensation of

quinaldine with aromatic aldehydes. Leishmanicidal activity was estimated for Leishmania panamensis at the amastigote form and cytotoxic activity against U-937 cells. All compounds showed activity against

both L. panamensis and U-937 cells. (E)-2-(2,5-dimethoxyphenyl)ethenyl)quinoline (1), (E)-2-(2,3-

dimethoxyphenyl)ethenyl)quinoline (2) and (E)-N-[4-(2-quinolin-2-yl-ethenyl)phenyl]acetamide (3)

were more active against axenic (EC50= 3.7, 4.5 and 19.1μg/mL) and intracellular amastigotes (EC50=

1.4, 1.8 and 1.7μg/ml, respectively), in comparison with hydrogenated derivatives 2-[2-(2,5-dimethoxy

phenyl)ethyl]quinoline (1a), 2-[2-(2,3-dimethoxyphenyl)ethyl]quinoline (2a) and N-[4-(2-quinolin-

2-ylethyl)phenyl]acetamide (3a) (CE50= 31.1, 23.6 and 59.3μg/mL, respectively). All compounds were

also active against the U-937 cells. Styrylquinolines 1, 2 and 3 showed a LC50 of 3.7, 6.2 and 4.5μg/mL,

respectively and the hydrogenated derivatives 1a, 2a and 3a showed a LC50 of 16.0. 12.9 and 20.2μg/mL,

respectively. Although hydrogenation reduced the leishmanicidal and cytotoxic activities, the activity

showed against Leishmania parasites suggests this compound series has potential as drug candidates for

the treatment of leishmaniasis.

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Published

17-02-2009

How to Cite

MESA, A. M., MOLANO M., P. A., SEON, B., FIGADERE, B., ROBLEDO, S. M., MUÑOZ, D. L., & SÁEZ V., J. A. (2009). SYNTHESIS AND IN VITRO LEISHMANICIDAL AND CYTOTOXIC ACTIVITIES OF 2-STYRYLQUINOLINES ANALOGS. Vitae, 15(2). https://doi.org/10.17533/udea.vitae.798

Issue

Section

Pharmacology and Toxicology

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