Trypanocidal activity of isolated naphthoquinones from Tabebuia and some heterocyclic derivatives: a review from an interdisciplinary study

Naphthoquinones isolated from the wood of trees of the families Bignoniaceae and Verbenaceae have been subjected to an interdisciplinary study since the seventies, when Dr. Benjamin Gilbert, at the Federal University of Rio de Janeiro, launched a program on the chemistry of natural products active a...

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Main Authors: De Moura Kelly C. G., Emery Flávio S., Neves-Pinto Cleverson, Pinto Maria do Carmo F. R., Dantas Andrea P., Salomão Kelly, Castro Solange L. de, Pinto Antônio V.
Format: Article
Language:English
Published: Sociedade Brasileira de Química 2001-01-01
Series:Journal of the Brazilian Chemical Society
Subjects:
Online Access:http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532001000300003
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author De Moura Kelly C. G.
Emery Flávio S.
Neves-Pinto Cleverson
Pinto Maria do Carmo F. R.
Dantas Andrea P.
Salomão Kelly
Castro Solange L. de
Pinto Antônio V.
author_facet De Moura Kelly C. G.
Emery Flávio S.
Neves-Pinto Cleverson
Pinto Maria do Carmo F. R.
Dantas Andrea P.
Salomão Kelly
Castro Solange L. de
Pinto Antônio V.
author_sort De Moura Kelly C. G.
collection DOAJ
description Naphthoquinones isolated from the wood of trees of the families Bignoniaceae and Verbenaceae have been subjected to an interdisciplinary study since the seventies, when Dr. Benjamin Gilbert, at the Federal University of Rio de Janeiro, launched a program on the chemistry of natural products active against endemic diseases. In this paper we describe the synthesis of five naphthoimidazoles, derived from this program and their activity towards T. cruzi, the etiologic agent of Chagas disease. We also review the influence of chemical structure on trypanocidal action of naphthoquinones and of derived heterocycles with imidazole, oxazole, phenoxazine, indole, dipyrane and cyclopentene rings. The overall analysis corroborates the tendency of trypanocidal activity in compounds with an imidazole or oxazole ring linked to a naphthopyrane structure. Two naphthoimidazoles presented higher activities (14.5x and 34.8x) than the standard crystal violet. Emphasis is given to the biodiversity of the Brazilian flora as a starting point for the development of an autonomous and creative medicinal chemistry.
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spelling doaj.art-b4d73be805314e27ad3e548d25d41c152022-12-22T00:49:41ZengSociedade Brasileira de QuímicaJournal of the Brazilian Chemical Society0103-50532001-01-01123325338Trypanocidal activity of isolated naphthoquinones from Tabebuia and some heterocyclic derivatives: a review from an interdisciplinary studyDe Moura Kelly C. G.Emery Flávio S.Neves-Pinto CleversonPinto Maria do Carmo F. R.Dantas Andrea P.Salomão KellyCastro Solange L. dePinto Antônio V.Naphthoquinones isolated from the wood of trees of the families Bignoniaceae and Verbenaceae have been subjected to an interdisciplinary study since the seventies, when Dr. Benjamin Gilbert, at the Federal University of Rio de Janeiro, launched a program on the chemistry of natural products active against endemic diseases. In this paper we describe the synthesis of five naphthoimidazoles, derived from this program and their activity towards T. cruzi, the etiologic agent of Chagas disease. We also review the influence of chemical structure on trypanocidal action of naphthoquinones and of derived heterocycles with imidazole, oxazole, phenoxazine, indole, dipyrane and cyclopentene rings. The overall analysis corroborates the tendency of trypanocidal activity in compounds with an imidazole or oxazole ring linked to a naphthopyrane structure. Two naphthoimidazoles presented higher activities (14.5x and 34.8x) than the standard crystal violet. Emphasis is given to the biodiversity of the Brazilian flora as a starting point for the development of an autonomous and creative medicinal chemistry.http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532001000300003naphthoquinonesheterocyclesTabebuiaTrypanosoma cruziChagas disease
spellingShingle De Moura Kelly C. G.
Emery Flávio S.
Neves-Pinto Cleverson
Pinto Maria do Carmo F. R.
Dantas Andrea P.
Salomão Kelly
Castro Solange L. de
Pinto Antônio V.
Trypanocidal activity of isolated naphthoquinones from Tabebuia and some heterocyclic derivatives: a review from an interdisciplinary study
Journal of the Brazilian Chemical Society
naphthoquinones
heterocycles
Tabebuia
Trypanosoma cruzi
Chagas disease
title Trypanocidal activity of isolated naphthoquinones from Tabebuia and some heterocyclic derivatives: a review from an interdisciplinary study
title_full Trypanocidal activity of isolated naphthoquinones from Tabebuia and some heterocyclic derivatives: a review from an interdisciplinary study
title_fullStr Trypanocidal activity of isolated naphthoquinones from Tabebuia and some heterocyclic derivatives: a review from an interdisciplinary study
title_full_unstemmed Trypanocidal activity of isolated naphthoquinones from Tabebuia and some heterocyclic derivatives: a review from an interdisciplinary study
title_short Trypanocidal activity of isolated naphthoquinones from Tabebuia and some heterocyclic derivatives: a review from an interdisciplinary study
title_sort trypanocidal activity of isolated naphthoquinones from tabebuia and some heterocyclic derivatives a review from an interdisciplinary study
topic naphthoquinones
heterocycles
Tabebuia
Trypanosoma cruzi
Chagas disease
url http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532001000300003
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