Horn A S, Grol C J, Dijkstra D, Mulder A H
J Med Chem. 1978 Aug;21(8):825-8. doi: 10.1021/jm00206a023.
The facile syntheses of important intermediates used in the preparation of the two potent dopaminergic argonists, 2-amino-6,7-dihydroxytetrahydronaphthalene (11) (referred to by some authors as ADTN) and its 5,6-dihydroxyl isomer 12, are described. Thus 6,7-dimethyoxy-2-tetralone has been prepared in two steps and 5,6-dimethoxy-2-tetralone in three steps both from commercially available materials. The effects of 11, 12, and the noncatechol analogue, 2-aminotetrahydronaphthalene (ATN), on radioactive neurotransmitter release have been studied in vitro using rat brain slices. It has been shown that both 11 and 12, at a concentraiton of 2 micron, cause a release of [3H]-DA and NA, 11 being more potent than 12 in releasing [3H]-DA. ATN (2 micron) was found to be inactive in these experiments which shows the importance of the catechol function in this uptake--release process.
本文描述了用于制备两种强效多巴胺能激动剂，即2-氨基-6,7-二羟基四氢萘（11）（一些作者称之为ADTN）及其5,6-二羟基异构体12的重要中间体的简便合成方法。因此，已从市售原料分两步制备了6,7-二甲氧基-2-四氢萘酮，分三步制备了5,6-二甲氧基-2-四氢萘酮。使用大鼠脑片在体外研究了11、12和非儿茶酚类似物2-氨基四氢萘（ATN）对放射性神经递质释放的影响。结果表明，在2微摩尔的浓度下，11和12均会导致[3H]-多巴胺（DA）和去甲肾上腺素（NA）的释放，在释放[3H]-DA方面，11比12更有效。在这些实验中发现ATN（2微摩尔）无活性，这表明儿茶酚官能团在这种摄取-释放过程中的重要性。
