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

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.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Tapia RA,Salas C,Morello A,Maya JD,Toro-Labbé A

doi

10.1016/j.bmc.2004.01.046

subject

Has Abstract

pub_date

2004-05-01 00:00:00

pages

2451-8

issue

9

eissn

0968-0896

issn

1464-3391

pii

S0968089604000896

journal_volume

12

pub_type

杂志文章

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