TY - JOUR
T1 - Synthesis and antitumor activity of quinonoid derivatives of cannabinoids
AU - Kogan, Natalya M.
AU - Rabinowitz, Ruth
AU - Levi, Paloma
AU - Gibson, Dan
AU - Sandor, Peter
AU - Schlesinger, Michael
AU - Mechoulam, Raphael
PY - 2004/7
Y1 - 2004/7
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=3142618434&partnerID=8YFLogxK
U2 - 10.1021/jm040042o
DO - 10.1021/jm040042o
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C2 - 15239658
AN - SCOPUS:3142618434
SN - 0022-2623
VL - 47
SP - 3800
EP - 3806
JO - Journal of Medicinal Chemistry
JF - Journal of Medicinal Chemistry
IS - 15
ER -
