Anti-plasmodial and anti-trypanosomal activity of synthetic naphtho[2,3-b]thiophen-4,9-quinones

Carlos L. Zani (Lead / Corresponding author), Egler Chiari, Antoniana U. Krettli, Silvane M.F. Murta, Mark L. Cunningham, Alan H. Fairlamb, Alvaro J. Romanha

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    71 Citations (Scopus)


    Naphtho[2,3-b]thiophen-4,9-quinone and five derivatives were prepared using the Friedel-Crafts reaction and tandem-lithiation of aromatic diethylamides. These quinones were evaluated for their trypanocidal and anti-plasmodial activities by their effects on: (1) growth of epimastigote forms of Trypanosoma cruzi in vitro, (2) lysis of trypomastigote forms of T. cruzi in murine blood, (3) growth of Plasmodium falciparum in vitro, and (4) inhibition of the recombinant enzyme trypanothione reductase. The parent compound, naphtho[2,3-b]thiophen-4,9-quinone (3a), was among the most active quinone tested in vitro against P. falciparum at 0.2 μM. However, it was inactive against P. berghei-infected mice treated with 2.3 mmol/kg daily for 5 days. Most of the quinones prepared were active against T. cruzi epimastigotes in culture but exhibited weak activity at 4°C against trypomastigotes in murine blood as well against the enzyme trypanothione reductase. Further structural modifications will be necessary to improve the in vivo activity of the naphthothiophenquinones.

    Original languageEnglish
    Pages (from-to)2185-2192
    Number of pages8
    JournalBioorganic and Medicinal Chemistry
    Issue number12
    Publication statusPublished - Dec 1997


    • Naphthothiophenquinones
    • Plasmodium berghei
    • Plasmodium falciparum
    • Trypanosoma cruzi
    • Trypanothione reductase

    ASJC Scopus subject areas

    • Biochemistry
    • Molecular Medicine
    • Molecular Biology
    • Pharmaceutical Science
    • Drug Discovery
    • Clinical Biochemistry
    • Organic Chemistry


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