9‐Alkoxy‐1, 5‐dichloroanthracenes were sucessfully prepared. Their cytotoxicity was evaluated in vitro on rat glioma C6 cell lines and human hepatoma G2 cell lines, respectively. Alkylation of 1, 5‐dichloro‐9(10H)‐anthracenone with either the appropriate alcohols or alkyl chlorides in the presence of sulfuric acid or sodium hydride, respectively, furnished this structural class of anthracenes. Contrary to mitoxantrone, cytotoxic properties were observed as documented by the reactivity of the novel compounds and potent in vitro activity against C6 cells and hep G2 cells over a wide range of structural variants. Among these compounds, 5c, 5h, 5land 5n are potent cytotoxins. They inhibit C6 cell growth in culture, indicated by using 2, 3‐bis(2‐methoxy‐4‐nitro‐5‐sulfophenyl)‐2H‐tetrazolium‐5‐carboxanilide sodium salt (XTT) colorimetric assay. By using this assay it was also shown that 5c, 5dand 5l possess potent cytotoxicity on hep G2 cells. The most active compound displaying in vitro cytotoxicity was the 9‐butoxy derivative 5hwith IC50 values 0.02 μM against C6 cells, as compared with mitoxantrone with IC50 values 0.07 μM. The most active compound displaying in vitro cytotoxicity against hep G2 cells was 5c with IC50 values 1.7 μM (mitoxantrone: 0.8 μM). Structure‐activity relationships (SAR) of these compounds with respect to the nature of the alkoxy substitution in the 9 position are discussed for both cell lines.

中文翻译：

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9-烷氧基-1, 5-二氯蒽衍生物在鼠和人培养肿瘤细胞中的合成和细胞毒性

9-Alkoxy-1, 5-二氯蒽制备成功。它们的细胞毒性分别在大鼠神经胶质瘤 C6 细胞系和人肝癌 G2 细胞系上进行了体外评估。在硫酸或氢化钠存在下，1, 5-二氯-9(10H)-蒽酮分别与适当的醇或烷基氯化物烷基化，提供了这种结构类型的蒽。与米托蒽醌相反，通过新化合物的反应性和针对 C6 细胞和 hep G2 细胞的有效体外活性在广泛的结构变体上观察到了细胞毒性特性。在这些化合物中，5c、5h、5和 5n 是有效的细胞毒素。通过使用 2, 3-双(2-甲氧基-4-硝基-5-磺苯基)-2H-四唑鎓-5-甲酰苯胺钠盐 (XTT) 比色测定，它们抑制培养中的 C6 细胞生长。通过使用该测定，还表明 5c、5d 和 5l 对 hep G2 细胞具有有效的细胞毒性。与米托蒽醌的 IC50 值为 0.07 μM 相比，表现出体外细胞毒性的最活性化合物是 9-丁氧基衍生物，其对 C6 细胞的 IC50 值为 0.02 μM。对 hep G2 细胞表现出体外细胞毒性的最活性化合物是 5c，IC50 值为 1.7 μM（米托蒽醌：0.8 μM）。讨论了这些化合物的构效关系 (SAR) 与 9 位烷氧基取代的性质有关的两种细胞系。07 微米。对 hep G2 细胞表现出体外细胞毒性的最活性化合物是 5c，IC50 值为 1.7 μM（米托蒽醌：0.8 μM）。讨论了这些化合物的构效关系 (SAR) 与 9 位烷氧基取代的性质有关的两种细胞系。07 微米。对 hep G2 细胞表现出体外细胞毒性的最活性化合物是 5c，IC50 值为 1.7 μM（米托蒽醌：0.8 μM）。讨论了这些化合物的构效关系 (SAR) 与 9 位烷氧基取代的性质有关的两种细胞系。