Superchi S, Pini D, Salvadori P, Marinelli F, Rainaldi G, Zanelli U, Nuti-Ronchi V
Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Italy.
Chem Res Toxicol. 1993 Jan-Feb;6(1):46-9. doi: 10.1021/tx00031a007.
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.
通过邻甲基苯甲酰胺的金属化反应，以高产率合成了二氢异香豆素（±）-6-甲氧基-8-羟基-3-甲基-3,4-二氢异香豆素（1）、（±）-6,8-二羟基-3-甲基-3,4-二氢异香豆素（2）和（±）-6,8-二甲氧基-3-甲基-3,4-二氢异香豆素（3）。对这些化合物以及从胡萝卜细胞中提取的（-）-1的毒性进行了体外测试，测试对象为中国仓鼠细胞。根据内酯羰基邻位羟基的有无以及二氢异香豆素的立体化学来确定毒性。
