新型芳姜黄酮拼合吡咯螺环氧化吲哚类化合物的合成及其抗肿瘤活性

摘要

Ten novel turmerone motif-fused spiropyrrolidine oxindoles(3a~3j) were synthesized by 1, 3-dipolar reaction of substituted isatins with sarcosine, then 3+2 cycloaddition with ( E)-dienones in MeCN.The yields and d/r of 3a~3j were 70%~91%and 15∶1~>20∶1, respectively.The struc-tures were characterized by 1 H NMR, 13 C NMR and HR-MS( ESI-TOF) .The in vitro antitumor activi-ties against human lung cancer cells(A549) and human leukemia cells(K562) were demonstrated by MTT assays.The results showed that 3f exhibited best activity against K562 with IC50 of 31.1 μmol· L-1 and 3b indicated best activity against A549 with IC50 of 54.1 μmol· L-1 .%以取代靛红和肌氨酸为原料制得1，3-偶极子，再与（ E）-芳姜烯酮类化合物在乙腈中经3＋2环加成反应合成了10个新型的芳姜黄酮拼合吡咯螺环氧化吲哚类化合物（3a～3j），产率70％～91％， d／r值15∶1～＞20∶1，其结构经1H NMR，13C NMR和HR-MS（ESI-TOF）表征。采用MTT法研究了3a～3j对人肺癌细胞（A549）和人白血病细胞（K562）的体外抗肿瘤活性。结果表明：3f对K562抑制活性较好（IC50＝31．1μmol· L－1），3b对A549抑制活性较好（ IC50＝54．1μmol· L－1）。