Anti-leishmanial and structure-activity relationship of ring substituted 3-phenyl-1-(1,4-di-N-oxide quinoxalin-2-yl)-2-propen-1-one derivatives

Anti-leishmanial and structure-activity relationship of ring substituted 3-phenyl-1-(1,4-di-N-oxide quinoxalin-2-yl)-2-propen-1-one derivatives

A series of ring substituted 3-phenyl-1-(1,4-di-N-oxide quinoxalin-2-yl)-2-propen-1-one derivatives were synthesized and tested for in vitro leishmanicidal activity against amastigotes of Leishmania amazonensis in axenical cultures and murine infected macrophages. Structure-activity relationships de...

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Bibliographic Details
Main Authors: Burguete, A. (Asunción), Estevez, Y. (Yannick), Castillo, D. (Denis), Gonzalez, G. (Germán), Raquel, Solano, B. (Beatriz), Vicente, E. (Esther), Pérez-Silanes, S. (Silvia), Aldana, I. (Ignacio), Monge, A. (Antonio), Sauvain, M. (Michel), Deharo, E. (Eric)
Format: info:eu-repo/semantics/article
Language:eng
Published: Instituto Oswaldo Cruz, Ministério da Saúde 2015
Subjects:
Quinoxaline
Anti-leishmanial
Structure-activity
Leishmaniasis
Online Access:https://hdl.handle.net/10171/37636
Description
Summary:A series of ring substituted 3-phenyl-1-(1,4-di-N-oxide quinoxalin-2-yl)-2-propen-1-one derivatives were synthesized and tested for in vitro leishmanicidal activity against amastigotes of Leishmania amazonensis in axenical cultures and murine infected macrophages. Structure-activity relationships demonstrated the importance of a radical methoxy at position R3', R4' and R5'. (2E)-3-(3,4,5-trimethoxy-phenyl)-1-(3,6,7-trimethyl-1,4-dioxy-quinoxalin-2-yl)-propenone was the most active. Cytotoxicity on macrophages revealed that this product was almost six times more active than toxic.

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