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1: J Med Chem. 2004 Jul 15;47(15):3800-6.Click here to read Links

Synthesis and antitumor activity of quinonoid derivatives of cannabinoids.

Kogan NM, Rabinowitz R, Levi P, Gibson D, Sandor P, Schlesinger M, Mechoulam R.

Department of Medicinal Chemistry and Natural Products, School of Pharmacy, The Hebrew University, Jerusalem 91120, Israel.

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.

PMID: 15239658 [PubMed - indexed for MEDLINE]

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