Synthesis and biological activity of 2-amino-1-oxa-2,3-dihydro-1-H-phenalene derivatives.

Drug design and delivery Pub Date : 1990-09-01
W Y Wang, J P Freeman, M A Burian, P F Vonvoigtlander, J Szmuszkovicz
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Abstract

The preparation of two 2-dialkylamino-1-oxa-2,3-dihydro-1H-phenalenes (3 and 4) is described. Lewis acid-catalyzed Baeyer-Villiger reaction of acenaphthenone (5) gave the lactone 6. Reduction afforded the lactol 7, which was reacted with amines to give the target compounds 3 and 4. Investigation of the effects of these compounds on catechol and indole metabolism revealed that they lack the dopamine antagonist or agonist and serotonin agonist properties of the respective deoxy analogues.

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2-氨基-1-氧-2,3-二氢-1- h -苯衍生物的合成及其生物活性。
介绍了两种2-二烷基氨基-1-氧-2,3-二氢- 1h -苯(3和4)的制备方法。Lewis酸催化苊酮(5)的Baeyer-Villiger反应得到内酯6。还原得到乳酸菌7,它与胺反应得到目标化合物3和4。对这些化合物对儿茶酚和吲哚代谢影响的研究表明,它们缺乏各自脱氧类似物的多巴胺拮抗剂或激动剂和血清素激动剂的特性。
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