Literature DB >> 12057662

Synthesis and preliminary pharmacological evaluation of new (+/-) 1,4-naphthoquinones structurally related to lapachol.

Alcides J M da Silva1, Camilla D Buarque, Flávia V Brito, Laure Aurelian, Luciana F Macedo, Linda H Malkas, Robert J Hickey, Daniele V S Lopes, François Noël, Yugo L B Murakami, Noelson M V Silva, Paulo A Melo, Rodrigo R B Caruso, Newton G Castro, Paulo R R Costa.   

Abstract

Seven new 1,4-naphthoquinones structurally related to lapachol were synthesized from lawsone and oxygenated arylmercurials. These compounds can also be seen as pterocarpan derivatives where the A-ring was substituted by the 1,4-naphthoquinone nucleus. Pharmacological screening provided evidence of significant biological activities, including effects against proliferation of the MCF-7 human breast cancer cell line, against Herpes Simplex Virus type 2 infection, and against snake poison-induced myotoxicity. One derivative displaced flunitrazepam binding and showed benzodiazepine-like activity, suggesting novel neuroactive structural motifs.

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Year:  2002        PMID: 12057662     DOI: 10.1016/s0968-0896(02)00100-1

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN: 0968-0896            Impact factor:   3.641


  7 in total

1.  Anticancer activity and SAR studies of substituted 1,4-naphthoquinones.

Authors:  Deepak Bhasin; Somsundaram N Chettiar; Jonathan P Etter; May Mok; Pui-Kai Li
Journal:  Bioorg Med Chem       Date:  2013-05-18       Impact factor: 3.641

2.  Comparison of the cytotoxic effect of lapachol, alpha-lapachone and pentacyclic 1,4-naphthoquinones on human leukemic cells.

Authors:  Eduardo J S Salustiano; Chaquip D Netto; Renata F Fernandes; Alcides J M da Silva; Thiago S Bacelar; Carolina P Castro; Camilla D Buarque; Raquel C Maia; Vivian M Rumjanek; Paulo R R Costa
Journal:  Invest New Drugs       Date:  2009-03-04       Impact factor: 3.850

3.  Genotoxicity of lapachol evaluated by wing spot test of Drosophila melanogaster.

Authors:  Wender Ferreira Costa; Alaide Braga de Oliveira; Júlio César Nepomuceno
Journal:  Genet Mol Biol       Date:  2010-09-01       Impact factor: 1.771

4.  Synthesis and pharmacological activity of diterpenylnaphthoquinone derivatives.

Authors:  Mariano Walter Pertino; Cristina Theoduloz; Jose Antonio Palenzuela; Maria del Mar Afonso; Erdem Yesilada; Francisco Monsalve; Paulo González; Daniel Droguett; Guillermo Schmeda-Hirschmann
Journal:  Molecules       Date:  2011-10-13       Impact factor: 4.411

5.  Ionically Crosslinked Chitosan Membranes Used as Drug Carriers for Cancer Therapy Application.

Authors:  Alecsandra Ferreira Tomaz; Sandra Maria Sobral de Carvalho; Rossemberg Cardoso Barbosa; Suédina M L Silva; Marcos Antônio Sabino Gutierrez; Antônio Gilson B de Lima; Marcus Vinícius L Fook
Journal:  Materials (Basel)       Date:  2018-10-20       Impact factor: 3.623

6.  Lapachol and synthetic derivatives: in vitro and in vivo activities against Bothrops snake venoms.

Authors:  Marcelo A Strauch; Marcelo Amorim Tomaz; Marcos Monteiro-Machado; Bruno Lemos Cons; Fernando Chagas Patrão-Neto; Jhonatha da Mota Teixeira-Cruz; Matheus da Silva Tavares-Henriques; Pâmella Dourila Nogueira-Souza; Sara L S Gomes; Paulo R R Costa; Edgar Schaeffer; Alcides J M da Silva; Paulo A Melo
Journal:  PLoS One       Date:  2019-01-28       Impact factor: 3.240

7.  A novel 1,4-naphthoquinone-derived compound induces apoptotic cell death in breast cancer cells.

Authors:  Didem Karakaş; Remzi Okan Akar; Zeliha Gökmen; Nahide Gülşah Deniz; Engin Ulukaya
Journal:  Turk J Biol       Date:  2019-08-05
  7 in total

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