Synthesis of dihydronaphthofurandiones and dihydrofuroquinolinediones with trypanocidal activity and analysis of their stereoelectronic properties

Tapia, RA; Salas C.; Morello A.; Maya, JD; Toro-Labbe, A

Abstract

The synthesis of dihydronaphthofurandione and dihydrofuroquinolinedione derivatives 4-11 was performed through Diels-Alder reactions of dihydrobenzofurandione 1 with several carbodienes and acrolein N,N-dimethylhydrazone. Then, the use of 5-bromobenzofurandione 2 toward 1,3-pentadiene and the 1-azadiene afforded quinones 6 and 11 with a total regioselectivity. All the prepared quinones were tested for trypanocidal activity in vitro against Trypanosoma epimastigotes, Tulahuen strain. Among the tested compounds, the furoquinolinediones 10 and 11 have shown potent trypanocidal activities but, only the 1,5-regioisomer (11) was found active as a redox cycling agent. Calculation of their stereoelectronic properties by the density-functional theory method provided a new insight for the trypanocidal activity of these heterocyclic quinones. © 2004 Elsevier Ltd. All rights reserved.

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Título según WOS: Synthesis of dihydronaphthofurandiones and dihydrofuroquinolinediones with trypanocidal activity and analysis of their stereoelectronic properties
Título según SCOPUS: Synthesis of dihydronaphthofurandiones and dihydrofuroquinolinediones with trypanocidal activity and analysis of their stereoelectronic properties
Título de la Revista: BIOORGANIC & MEDICINAL CHEMISTRY
Volumen: 12
Número: 9
Editorial: PERGAMON-ELSEVIER SCIENCE LTD
Fecha de publicación: 2004
Página de inicio: 2451
Página final: 2458
Idioma: English
URL: http://linkinghub.elsevier.com/retrieve/pii/S0968089604000896
DOI:

10.1016/j.bmc.2004.01.046

Notas: ISI, SCOPUS