To search for new biological activities of the chromeno[2,3-b]indoles, the 5-oxa analog of the indolo[2,3-b]quinolines that are known to have a potent antitumor activity, a series of 11-amino derivatives with various substituents at the C-2 position were prepared. The synthesis of the chromeno[2,3-b]indole structure involves the cyclization of 2-phenoxy-3-indolecarboxylates 3, accessible from the indole-3-carboxylate 1 and phenols 2, producing the chromeno[2,3-b]indol-11(6H)-ones 4, which is followed by dehydroxychlorination with phosphorus oxychloride to afford the 11-chlorochromeno[2,3-b]indoles 5. The treatment of 5 with various amines produced the corresponding 11-aminated chromeno[2,3-b]indoles 6, while some of the 11-ω-aminoalkylamino derivatives 6 were transformed into the 11-ω-sulfonylaminoalkylamino derivatives 8. The antiproliferative activity of these 11-aminochromeno[2,3-b]indoles 6 and 8 in vitro were tested using MV4-11 (human leukemia), A549 (lung cancer), HCT116 (colon cancer), and the normal mice fibroblast (BALB/3T3) and their potencies were described.

译文

:为了寻找新的色素沉着[2,3-b]吲哚的生物活性,吲哚[2,3-b]喹啉的5-氧杂类似物已知具有强大的抗肿瘤活性,一系列的11-制备在C-2位具有各种取代基的氨基衍生物。 chromeno [2,3-b]吲哚结构的合成涉及2-苯氧基-3-吲哚羧酸酯3(可从吲哚-3-羧酸酯1和酚2进入)的环化,从而生成chromeno [2,3-b] indol-11(6H)-ones 4,然后用三氯氧化磷进行脱羟基氯化,得到11-氯铬色[2,3-b]吲哚5。用各种胺处理5产生相应的11-胺化铬色[2] ,3-b]吲哚6,而一些11-ω-氨基烷基氨基吲哚6被转化为11-ω-磺酰基氨基烷基氨基衍生物8。这些11-氨基色酚[2,3-b]吲哚6和8的抗增殖活性在体外使用MV4-11(人类白血病),A549(肺癌),HCT116(结肠癌)和正常小鼠成纤维细胞(BALB / 3T3)进行了测试,并对其效力进行了描述。

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