Insights into the structural patterns of the antileishmanial activity of bi- and tricyclic N-heterocycles

The influence of various structural patterns in a series of novel bi- and tricyclic N-heterocycles on the activity against Leishmania major and Leishmania panamensis has been studied and compounds that are active in the low micromolar region have been identified. Both quinolines and tetrahydrooxazin...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2016-01, Vol.14 (29), p.753-76
Main Authors: Herrera, Lizzi, Stephens, David E, D'Avila, Abigail, George, Kathryn G, Arman, Hadi, Zhang, Yu, Perry, George, Lleonart, Ricardo, Larionov, Oleg V, Fernández, Patricia L
Format: Article
Language:English
Subjects:
Animals
Antiprotozoal Agents - chemistry
Antiprotozoal Agents - pharmacology
Crystallography, X-Ray
Dose-Response Relationship, Drug
Heterocyclic Compounds - chemistry
Heterocyclic Compounds - pharmacology
Interleukin-10 - antagonists & inhibitors
Interleukin-10 - biosynthesis
Leishmania - drug effects
Leishmania major
Leishmania panamensis
Macrophages - drug effects
Macrophages - metabolism
Mice
Mice, Inbred BALB C
Models, Molecular
Molecular Structure
Parasitic Sensitivity Tests
Structure-Activity Relationship
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Summary:The influence of various structural patterns in a series of novel bi- and tricyclic N-heterocycles on the activity against Leishmania major and Leishmania panamensis has been studied and compounds that are active in the low micromolar region have been identified. Both quinolines and tetrahydrooxazinoindoles (TOI) proved to have significant antileishmanial activities, while substituted indoles were inactive. We have also showed that a chloroquine analogue induces Leishmania killing by modulating macrophage activation. Synthesis and discovery of new 1,2-oxazine-containing heterocycles with antileishmanial activity is described.
ISSN:1477-0520
1477-0539
DOI:10.1039/c6ob01149g