Synthesis and toxicity to mammalian cells of the carrot dihydroisocoumarins.
The dihydroisocoumarins (+-)-6-methoxy-8-hydroxy-3-methyl-3,4- dihydroisocoumarin (1), (+-)-6,8-dihydroxy-3-methyl-3,4-dihydroisocoumarin (2), and (+-)-6,8-dimethoxy-3-methyl-3,4-dihydroisocoumarin (3) were synthesized with high yields via metalation of o-methylbenzamides. The toxicity of these compounds and that of (-)-1 extracted from carrot cells were tested, in vitro, on Chinese hamster cells. The toxicity was determined according to the presence or absence of a hydroxyl group in the peri position of the lactonic carbonyl group and according to the stereochemistry of the dihydroisocoumarin.
Superchi
S
S
Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Italy.
Pini
D
D
Salvadori
P
P
Marinelli
F
F
Rainaldi
G
G
Zanelli
U
U
Nuti-Ronchi
V
V
D000818:Animals; D002460:Cell Line; D002478:Cells, Cultured; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D006224:Cricetinae; D003412:Cricetulus; D007202:Indicators and Reagents; D049934:Isocoumarins; D009682:Magnetic Resonance Spectroscopy; D010944:Plants / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism; D000094162:Phytoalexins
D003374:Coumarins; D007202:Indicators and Reagents; D049934:Isocoumarins; C080190:6-methoxy-8-hydroxy-3-methyl-3,4-dihydroisocoumarin; D000094162:Phytoalexins; C070622:6-hydroxymellein; C080191:6,8-dimethoxy-3-methyl-3,4-dihydroisocoumarin