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,~(13)C 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))。
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 .