Synthesis, antileishmanial activity and QSAR studies of 2-chloro- N -arylacetamides

We describe herein the synthesis and evaluation of the antileishmanial activity against promastigote forms of Leishmania amazonensis and cytotoxicity to murine macrophages of a series of 2-chloro-N-arylacetamide derivatives. All compounds were active, except one (compound 3). Compound 5 presented th...

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Published inBrazilian Journal of Pharmaceutical Sciences Vol. 53; no. 1
Main Authors Lavorato, Stefânia Neiva, Duarte, Mariana Costa, Andrade, Pedro Henrique Rocha De, Coelho, Eduardo Antonio Ferraz, Alves, Ricardo José
Format Journal Article
LanguageEnglish
Portuguese
Published Sao Paulo Universidade de Sao Paulo Faculdade de Ciencias 01.01.2017
Universidade de São Paulo, Faculdade de Ciências Farmacêuticas
Universidade de São Paulo
Subjects
Biological activity
Chloroacetamides
Cytotoxicity
Enzymes
Leishmania amazonensisChloroacetamides/QSAR
Leishmaniasis/treatment
Parasites
Parasitic diseases
PHARMACOLOGY & PHARMACY
Tropical diseases
Leishmaniasis/treatment
Leishmania amazonensisChloroacetamides/QSAR
Chloroacetamides
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Summary:We describe herein the synthesis and evaluation of the antileishmanial activity against promastigote forms of Leishmania amazonensis and cytotoxicity to murine macrophages of a series of 2-chloro-N-arylacetamide derivatives. All compounds were active, except one (compound 3). Compound 5 presented the most promising results, showing good antileishmanial activity (CI50=5.39±0.67 µM) and moderate selectivity (SI=6.36), indicating that further development of this class is worthwhile. Preliminary QSAR studies, although not predictive, furnished some insights on the importance of electronic character of aryl substituent to biological activity, as well as an indirect influence of hydrophobicity on activity.
ISSN:1984-8250
2175-9790
1984-8250
2175-9790
DOI:10.1590/s2175-97902017000116067