Synthesis and Anti-human Leukemia Cells Activities of Novel Dehydroxylone/Tulipin A-based Spirooxindole Hybrids
Developing a diverse derivative library of privileged natural product frameworks is an impor-tant topic in natural organic chemistry.In this paper,we uses proline,isatins and dehydroxylone/tu-lipin A as starting materials,the reaction undergoes a[3+2]cycloaddition reaction and then N-oxida-tion reaction,intramolecular 1,2-migration-triggered ring expansion reaction to provide 8 dehydroxy-lone/tulipalin A-based spirooxindole hybrids(4a～4h)in 43％～63％overall yields and up to dr＞20∶1.The structures of products 4 were characterized by 1H NMR,13 C NMR and HR-MS(ESI-TOF).The relative configuration of compound 4e was further determined by single crystal X-ray dif-fraction.The in vitro antitumor activities against human leukemia cells(K562)were demonstrated by MTT assays using the commercially available broad-spectrum anticancer drug Cisplatin as a positive control.The results showed that dehydroxylone-based spirooxindole hybrids(4b,4c)and tulipin A-based spirooxindole hybrids(4f,4g)showed good cytotoxic effects.
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