Mixed steroidal 1,2,4,5-tetraoxanes: antimalarial and antimycobacterial activity (Articolo in rivista)

Type
Label
  • Mixed steroidal 1,2,4,5-tetraoxanes: antimalarial and antimycobacterial activity (Articolo in rivista) (literal)
Anno
  • 2002-01-01T00:00:00+01:00 (literal)
Alternative label
  • Solaja BA, Terzic N, Pocsfalvi G, Gerena L, Tinant B, Opsenica D, Milhous WK. (2002)
    Mixed steroidal 1,2,4,5-tetraoxanes: antimalarial and antimycobacterial activity
    in Journal of medicinal chemistry
    (literal)
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  • Solaja BA, Terzic N, Pocsfalvi G, Gerena L, Tinant B, Opsenica D, Milhous WK. (literal)
Pagina inizio
  • 3331 (literal)
Pagina fine
  • 3336 (literal)
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  • Brevetto internazionale: MIXED STEROIDAL 1,2,4,5-TETRAOXANE COMPOUNDS AND METHOD OF MAKING AND USING THEREOF, International application number: WO 03/068736 A2; Brevetto USA: MIXED STEROIDAL 1,2,4,5-TETRAOXANE COMPOUNDS AND METHOD OF MAKING AND USING THEREOF, “United States Patent Application Publication” Pub. No. US 2004/0019200 A1, pub date: jan.29, 2004 (literal)
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  • 45 (literal)
Rivista
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  • Sono stati preparati 1,2,4,5-tetraossani misti con sostituenti derivati da spirocicloalcani e acidi spirocolici che presentavano un’attività antimalarica maggiore dei tetraossani bi-sostituiti. Su 42 tetraossani sintetizzati, 12 si sono dimostrati più potenti dell’artemisinina contro il clone W2 cloroquina resistente Plasmodium falciparum e 9 più efficaci della cloroquina stessa contro il clone D6 cloroquina-suscettibile P. falciparum. E’ stata poi determinata la citotossicità per i composti più potenti contro la linea cellulare Vero, mostrando un rapporto tra la potenza citotossica e quella antimalarica di 1/(1400-9500). Per la prima volta, inoltre, i tetraossani sono stati testati contro il ceppo H37Rv di Mycobacterium tuberculosis con un MICs di 4.73 microM. (literal)
Note
  • ISI Web of Science (WOS) (literal)
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  • B. A. Šolaja, N. Terziæ, G. Pocsfalvi, L. Gerena, B. Tinant, D. Opsenica, W. K. Milhous Faculty of Chemistry, University of Belgrade, Yugoslavia, Istituto di Scienze dell'Alimentazione, CNR Avellino, Italy, Institute of Chemistry, Technology and Metallurgy, Belgrade, Yugoslavia, Laboratoire de Chimie Physique et de Cristallographie, Université Catholique de Louvain, Belgium, Division of Experimental Therapeutics, Walter Reed Army Institute of Research, Washington (literal)
Titolo
  • Mixed steroidal 1,2,4,5-tetraoxanes: antimalarial and antimycobacterial activity (literal)
Abstract
  • Mixed 1,2,4,5-tetraoxanes possessing simple spirocycloalkane and spirocholic acid-derived substituents were prepared and shown to have significantly higher in vitro antimalarial activity than bis-substituted tetraoxanes. Out of 41 synthesized tetraoxanes, 12 were in vitro more potent against Plasmodium falciparum chloroquine-resistant W2 clone than artemisinin, and the most potent one was 2.4 times as active as arteether. In addition, 9 compounds exhibit higher activity than chloroquine against P. falciparum chloroquine-susceptible D6 clone. Cytotoxicity was assessed for most active compounds against the Vero cell line, showing a cytotoxicity/antimalarial potency ratio of 1/(1400-9500). For the first time, tetraoxanes were screened against Mycobacterium tuberculosis with MICs as low as 4.73 microM against H37Rv strain. Mixed tetraoxanes were synthesized in a simple procedure from cholic acid methyl esters by direct coupling of steroidal gem-dihydroperoxide to simple ketones and further transformed into corresponding acids and amides. (literal)
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