This study describes the direct synthesis of 2-amino-4-(phenylsubstituted)-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives 5–21, through sequential multicomponent reaction of aromatic aldehydes, malononitrile, and 1-indanone in the presence of ammonium acetate and acetic acid (catalytic). The biological study showed that compound 10 significantly impeded proliferation of the cell lines PC-3, LNCaP, and MatLyLu. The antimetastatic effects of compound 10 could be related with inhibition of MMP9 in the PC-3 and LNCaP human cell lines. On the basis of a study of the structure–activity relationship of these compounds, we propose that the presence of two methoxy groups at positions 6 and 7 of the indeno nucleus and a 4-hydroxy-3-methoxy phenyl substitution pattern at position 4 of the pyridine ring is decisive for these types of molecules to exert very good antiproliferative and antimetastatic activities.

中文翻译：

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5H-茚并[1,2-b]吡啶衍生物的合成：对两种人前列腺癌细胞系的抗增殖和抗转移活性

该研究描述了2-氨基-4-（phenylsubstituted）-5-直接合成ħ -茚并[1,2- b ]吡啶-3-甲腈衍生物5 - 21，通过芳香醛，丙二腈，和1的顺序的多组分反应-在乙酸铵和乙酸（催化）存在下的茚满酮。生物学研究表明，化合物10显着阻碍了细胞系 PC-3、LNCaP 和 MatLyLu 的增殖。化合物10的抗转移作用可能与 PC-3 和 LNCaP 人细胞系中 MMP9 的抑制有关。在研究这些化合物的构效关系的基础上，我们提出茚核的 6 和 7 位存在两个甲氧基，而茚核的 4 位存在 4-羟基-3-甲氧基苯基取代模式。吡啶环是这些类型分子发挥非常好的抗增殖和抗转移活性的决定性因素。