Synthesis and antitumor activity of quinonoid derivatives of cannabinoids

Natalya M. Kogan, Ruth Rabinowitz, Paloma Levi, Dan Gibson, Peter Sandor, Michael Schlesinger, Raphael Mechoulam*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

95 Scopus citations

Abstract

Three cannabis constituents, cannabidiol (1), Δ8 -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.

Original languageAmerican English
Pages (from-to)3800-3806
Number of pages7
JournalJournal of Medicinal Chemistry
Volume47
Issue number15
DOIs
StatePublished - Jul 2004

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