Document Report Card

ID: ALA1148368

Journal: J Med Chem

Title: Synthesis and antitumor activity of quinonoid derivatives of cannabinoids.

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

Abstract: 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.

CiteXplore: 15239658

DOI: 10.1021/jm040042o