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Synthesis and antitumor activity of quinonoid derivatives of cannabinoids.
Kogan, Natalya M; Rabinowitz, Ruth; Levi, Paloma; Gibson, Dan; Sandor, Peter; Schlesinger, Michael; Mechoulam, Raphael.
Afiliación
  • Kogan NM; Department of Medicinal Chemistry and Natural Products, School of Pharmacy, The Hebrew University, Jerusalem 91120, Israel.
J Med Chem ; 47(15): 3800-6, 2004 Jul 15.
Article en En | MEDLINE | ID: mdl-15239658
Three cannabis constituents, cannabidiol (1), Delta(8)-tetrahydrocannabinol (3), and cannabinol (5), were oxidized to their respective para-quinones 2, 4, and 6. In the 1960s, the oxidized product 4 had been assigned a para-quinone structure, which was later modified to an ortho-quinone. To distinguish between the two possible quinone structures, a detailed NMR investigation was undertaken. The original para-quinone structure was confirmed. X-ray crystallography elucidated the structures of the crystalline 2 and 6. All three compounds displayed antiproliferative activity in several human cancer cell lines in vitro, and quinone 2 significantly reduced cancer growth of HT-29 cancer in nude mice.
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Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Quinonas / Cannabinoides / Antineoplásicos Límite: Animals / Humans Idioma: En Revista: J Med Chem Asunto de la revista: QUIMICA Año: 2004 Tipo del documento: Article País de afiliación: Israel Pais de publicación: Estados Unidos
Buscar en Google
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PubMed Links

Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Quinonas / Cannabinoides / Antineoplásicos Límite: Animals / Humans Idioma: En Revista: J Med Chem Asunto de la revista: QUIMICA Año: 2004 Tipo del documento: Article País de afiliación: Israel Pais de publicación: Estados Unidos