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首页> 外文期刊>European Journal of Medicinal Chemistry: Chimie Therapeutique >Structure-activity relationship studies of acridones as potential antipsoriatic agents. 1. Synthesis and antiproliferative activity of simple N-unsubstituted 10H-acridin-9-ones against human keratinocyte growth.
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Structure-activity relationship studies of acridones as potential antipsoriatic agents. 1. Synthesis and antiproliferative activity of simple N-unsubstituted 10H-acridin-9-ones against human keratinocyte growth.

机译：cri啶酮作为潜在的抗银屑病药物的构效关系研究。 1.简单的N-未取代的10H-acridin-9-ones的合成及其抗人角质形成细胞生长的活性。

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摘要

A series of N-unsubstituted hydroxy-10H-acridin-9-ones were synthesized and evaluated for inhibitory action against HaCaT keratinocyte growth, in order to explore their potential as antipsoriatic agents. For structure-activity relationship studies, the number and position of the hydroxyl groups were modified, the oxygen functions substituted or replaced, or additional functional groups were introduced into the acridone scaffold. 1,8-Dihydroxy-10H-acridin-9-one (4), which is an aza-analogue of the antipsoriatic anthralin, was only marginally active. However, 1,3-dihydroxy-substituted 5ee was the most potent acridone within this series and inhibited keratinocyte growth with an IC(50) value comparable to that of anthralin. In contrast to anthralin, nearly all members of the acridone series were devoid of radical generating properties, which were determined by their capability to interact with the free radical 2,2-diphenyl-1-picrylhydrazyl. Structures with a phenolic hydroxyl or an aromatic amine arranged ortho or para to the acridone NH group were exceptions. Also in contrast to anthralin, membrane-damaging effects as documented by the release of lactate dehydrogenase into the culture medium were not observed for acridones.
机译：合成了一系列N-未取代的羟基-10H--啶9-9-酮，并评估了其对HaCaT角质形成细胞生长的抑制作用，以探索其作为抗银屑病药物的潜力。为了研究结构活性关系，对羟基的数量和位置进行了修饰，氧官能团被取代或取代，或将其他官能团引入了a啶酮支架中。 1,8-二羟基-10H-ac啶9-9-（4）是一种抗银屑病蒽林的氮杂类似物，仅具有少量活性。但是，1,3-二羟基取代的5ee是该系列中最有效的a啶酮，其抑制角质形成细胞的生长的IC（50）值可与蒽林相当。与蒽林相反，a啶酮系列的几乎所有成员都没有自由基产生性质，这是由它们与自由基2，2-二苯基-1-picylhydrazyl相互作用的能力决定的。具有与hydroxyl啶酮NH基邻位或对位排列的酚羟基或芳族胺的结构是例外。同样与蒽醌相反，对于cri啶酮未观察到乳酸脱氢酶释放到培养基中所证明的膜破坏作用。

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