title: Synthesis and toxicity to mammalian cells of the carrot dihydroisocoumarins.
abstract: 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.
authors.affiliation: Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Italy.
authors.forename: S
authors.initials: S
authors.lastname: Superchi
authors.forename: D
authors.initials: D
authors.lastname: Pini
authors.forename: P
authors.initials: P
authors.lastname: Salvadori
authors.forename: F
authors.initials: F
authors.lastname: Marinelli
authors.forename: G
authors.initials: G
authors.lastname: Rainaldi
authors.forename: U
authors.initials: U
authors.lastname: Zanelli
authors.forename: V
authors.initials: V
authors.lastname: Nuti-Ronchi
mesh_terms: 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
chemical_list: 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